Desymmetrization of 2,4,5,6-Tetra-O-benzyl-D-myo-inositol for the Synthesis of Mycothiol
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1 Desymmetrization of 2,4,5,6-Tetra--benzyl-D-myo-inositol for the Synthesis of Mycothiol Chuan-Chung Chung, Medel Manuel L. Zulueta, Laxmansingh T. Padiyar, and Shang-Cheng Hung* Genomics Research Center, Academia Sinica, 128, Section 2, Academia Road, Taipei 11529, Taiwan and Department of Applied Chemistry, National Chiao Tung University, 1001, Ta Hsueh Road, Hsinchu 300 Taiwan SUPPRTING INFRMATIN General Procedures. Dichloromethane, tetrahydrofuran (THF), and acetonitrile were purified and dried from a safe purification system filled with anhydrous Al 2 3. Flash column chromatography was carried out on Silica Gel 60 ( mesh, E. Merk). TLC was performed on pre-coated glass plates of Silica Gel 60 F254 (0.25 mm, E. Merck); detection was executed by spraying with a solution of Ce(NH 4 ) 2 (N 3 ) 6, (NH 4 ) 6 Mo 7 24, and H 2 S 4 in water and subsequent heating on a hot plate. 1 H and 13 C NMR spectra were recorded on 600 MHz spectrometer. Chemical shifts are in ppm from Me 4 Si, calibrated using the residual proton and carbon of the deuterated solvent. Proton peak assignments were performed using 2D NMR techniques ( 1 H- 1 H CSY, HMQC and NESY); the hydrogen multiplicity of carbon peaks were determined using DEPT experiments. Bn Bn Bn Bn H H 7 Cl, DMAP pyr., 40 C, 24 h Bn Bn Bn Bn H 6: 69% + Bn Bn Bn Bn H 8: 24% + Bn Bn Bn Bn 9: 0% S1
2 2,4,5,6-tetra--benzyl-3--(1S)-ketopinyl-D-myo-inositol (6). (1S)-Ketopinyl chloride (21 mg, mmol) was added to a solution of the 1,3-diol 7 (51 mg, mmol) and N,Ndimethyl-4-aminopyridine (DMAP, 1 mg, mmol) in anhydrous pyridine (2 ml) at 40 C under nitrogen atmosphere. After stirring for 24 hours at the same temperature, water (5 ml) was added to the mixture followed by extraction with CH 2 Cl 2 (3 10 ml). The combined organic layer was dried over anhydrous MgS 4, filtered, and concentrated in vacuo. Purification of the residue via flash column chromatography (ethyl acetate/hexanes = 1/4) on silica gel gave compound 6 (46 mg, 69%), together with its regioisomer 8 (16 mg, 24 %). [ ] 28 D +5.1 (c 3.0, CHCl 3 ); IR (CHCl 3 ) 3449, 3030, 2954, 2883, 1751, 1721, 1453 cm 1 ; 1 H NMR (600 MHz, CDCl 3 ) (m, 8H, Ar-H), (m, 9H, Ar-H), (m, 3H, Ar-H), 5.05 (dd, J = 10.3, 2.5 Hz, 1H, H-3), 4.90 (d, J = 11.2 Hz, 1H, CH 2 Ar), (m, 4H, CH 2 Ar), (m, 3H, CH 2 Ar), 4.12 (t, J = 2.3 Hz, 1H, H-2), 4.10 (t, J = 9.5 Hz, 1H, H-4), 3.84 (t, J = 9.5 Hz, 1H, H-6), 3.65 (dd, J = 9.6, 2.2 Hz, 1H, H-1), 3.58 (t, J = 9.2 Hz, 1H, H-5), 2.50 (dt, J = 18.4, 3.6 Hz, 1H, CH 2 ), (m, 1H, CH 2 ), 2.15 (brs, 1H, 1- H), 2.05 (t, J = 4.4 Hz, 1H, CH), (m, 2H, CH 2 ), (m, 1H, CH 2 ), (m, 1H, CH 2 ), 1.13 (s, 3H, CH 3 ), 0.94 (s, 3H, CH 3 ); 13 C NMR (150 MHz, CDCl 3 ) (C), (C), (C), (C 2), (C), (CH 2), (CH 2), (CH 2), (CH 2), (CH 2), (CH), (CH 2), (CH), (CH), (CH 2), (CH 2), (CH), 83.7 (CH), 81.8 (CH), 79.3 (CH), 78.3 (CH), 75.7 (CH 2 ), 75.5 (CH 2 ), 75.2 (CH 2 ), 74.9 (CH 2 ), 73.9 (CH), 72.2 (CH), 68.1 (C), 49.2 (C), 44.3 (CH), 43.8 (CH 2 ), 26.5 (CH 2 ), 26.3 (CH 2 ), 21.3 (CH 3 ), 19.6 (CH 3 ); HRMS (ESI, MNa + ) calcd for C 44 H 48 8 Na , found ,4,5,6-tetra--benzyl-1--(1S)-ketopinyl-D-myo-inositol (8). [ ] 28 D +4.4 (c 5.0, CHCl 3 ); IR (CHCl 3 ) 3462, 3031, 2954, 2883, 1752, 1724, 1454 cm 1 ; 1 H NMR (600 MHz, CDCl 3 ) (m, 4H, Ar-H), (m, 4H, Ar-H), (m, 12H, Ar-H), 5.06 (dd, J = 10.3, 2.5 Hz, 1H, H-1), 4.90 (d, J = 11.2 Hz, 1H, CH 2 Ar), 4.89 (d, J = 11.4 Hz, 1H, CH 2 Ar), (m, 3H, CH 2 Ar), (m, 3H, CH 2 Ar), 4.15 (t, J = 2.5 Hz, 1H, H-2), 4.10 (t, J = 9.8 Hz, 1H, H-6), 3.84 (t, J = 9.5 Hz, 1H, H-4), 3.65 (dd, J = 9.7, 2.6 Hz, 1H, H-3), 3.57 (t, J = 9.2 Hz, 1H, H-5), 2.50 (dt, J = 18.4, 3.4 Hz, 1H, CH 2 ), (m, 2H, CH 2, 1-H), 2.04 (t, J = 4.3 Hz, 1H, CH), (m, 2H, CH 2 ), (m, 1H, CH 2 ), (m, 1H, CH 2 ), 1.18 (s, 3H, CH 3 ), 0.97 (s, 3H, CH 3 ); 13 C NMR (150 MHz, CDCl 3 ) (C), (C), (C), (C), (C), (C), (CH 2), S2
3 128.3 (CH 2), (CH 2), (CH 2), (CH 2), (CH 2), (CH), (CH 2), (CH), (CH), (CH 2), 83.5 (CH), 82.0 (CH), 79.5 (CH), 78.3 (CH), 75.8 (CH 2 ), 75.5 (CH 2 ), 75.3 (CH 2 ), 75.2 (CH 2 ), 73.7 (CH), 72.2 (CH), 67.8 (C), 48.9 (C), 44.0 (CH), 43.8 (CH 2 ), 26.3 (CH 2 ), 26.2 (CH 2 ), 21.0 (CH 3 ), 19.5 (CH 3 ); HRMS (ESI, MNa + ) calcd for C 44 H 48 8 Na , found ,4,5,6-tetra--benzyl-1,3-di--(1S)-ketopinyl-D-myo-inositol (9). [ ] 28 D (c 1.8, CHCl 3 ); IR (CHCl 3 ) 3030, 2966, 2883, 1753, 1727, 1454 cm 1 ; 1 H NMR (600 MHz, CDCl 3 ) 7.46 (d, J = 7.4 Hz, 2H, Ar-H), (m, 4H, Ar-H), (m, 7H, Ar-H), (m, 5H, Ar-H), (m, 2H, Ar-H), 5.26 (dd, J = 10.1, 2.0 Hz, 1H, H-1), 5.24 (dd, J = 10.1, 2.0 Hz, 1H, H-3), 4.99 (d, J = 11.2 Hz, 1H, CH 2 Ar), 4.95 (d, J = 10.7 Hz, 1H, CH 2 Ar), (m, 1H, CH 2 Ar), 4.92 (d, J = 10.7 Hz, 1H, CH 2 Ar), 4.88 (s, 2H, CH 2 Ar), 4.85 (d, J = 11.2 Hz, 1H, CH 2 Ar), 4.84 (d, J = 11.2 Hz, 1H, CH 2 Ar), 4.32 (s, 1H, H-2), (m, 2H, H-4, H-6), 3.75 (t, J = 9.3 Hz, 1H, H-5), (m, 2H, CH 2 ), (m, 1H, CH 2 ), (m, 1H, CH 2 ), (m, 2H, CH), (m, 2H, CH 2 ), 1.97 (dd, J = 18.4, 4.9 Hz, 2H, CH 2 ), (m, 2H, CH 2 ), (m, 2H, CH 2 ), 1.25 (s, 3H, CH 3 ), 1.21 (s, 3H, CH 3 ), (s, 6H, CH 3 ); 13 C NMR (150 MHz, CDCl 3 ) (C), (C), (C), (C), (C), (C), (C), (C), (CH 2), (CH 2), (CH 2), (CH 2), (CH 2), (CH), (CH 2), (CH), (CH 2), (CH 2), (CH 2), 83.5 (CH), 79.2 (CH), 79.0 (CH), 77.4 (CH), 75.8 (CH 2 ), 75.2 (CH 2 ), 75.1 (CH 2 ), 74.9 (CH 2 ), 73.1 (CH), 73.0 (CH), 67.8 (C), 67.5 (C), 49.0 (C), 48.8 (C), 44.1 (CH), 43.8 (CH), 43.6 (CH 2 2), 26.4 (CH 2 2), 26.2 (CH 2 2), 21.0 (CH 3 ), 20.9 (CH 3 ), 19.5 (CH 3 ), 19.4 (CH 3 ); HRMS (ESI, MNa + ) calcd for C 54 H Na , found NAP p-brbn TBDPS + N 3 STol 5 Bn Bn Bn Bn H 6 NIS, TfH CH 2 Cl 2, 60 C 3 h, 84% 2-NAP p-brbn TBDPS Bn Bn N 3 Bn Bn [2-Azido-3--(4-bromobenzyl)-6--tert-butyldiphenylsilyl-2-deoxy-4--(2- naphthylmethyl)- -D-glucopyranosyl]-2,4,5,6-tetra--benzyl-3--(1S)-ketopinyl-D-myoinositol (10). A solution of the donor 5 (150 mg, mmol) and the acceptor 6 (82 mg, mmol) in anhydrous dichloromethane (4 ml) containing freshly dried 4 Å molecular sieves (348 mg) was stirred at room temperature for 30 minutes under nitrogen atmosphere. S3
4 The solution was cooled to 60 C, and N-iodosuccinimide (NIS, 31 mg, mmol) was added to the reaction flask followed by TfH (5 L, mmol) 10 min later, and the solution was kept stirring at 60 C for 3 hours. Saturated NaHC 3 (10 ml) and 10% Na 2 S 2 3(aq) (10 ml) were added to quench the reaction, and the mixture was filtered through Celite and extracted with CH 2 Cl 2 (3 20 ml). The combined organic layer was dried over anhydrous MgS 4, filtered, and concentrated in vacuo. Purification of the residue via flash column chromatography (ethyl acetate/hexanes = 1/6) on silica gel furnished the desired adduct 10 (141 mg, 84%). [ ] 28 D +1.0 (c 2.5, CHCl 3 ); IR (CHCl 3 ) 3030, 2930, 2858, 2108, 1753, 1726, 1454 cm 1 ; 1 H NMR (600 MHz, CDCl 3 ) (m, 1H, Ar-H), (m, 2H, Ar-H), (m, 4H, Ar-H), (m, 1H, Ar-H), (m, 2H, Ar-H), (m, 21H, Ar-H), (m, 8H, Ar-H), (m, 2H, Ar-H), 5.42 (d, J = 3.6 Hz, 1H, H-1'), 5.00 (d, J = 10.6 Hz, 1H, CH 2 Ar), 4.97 (dd, J = 10.4, 2.3 Hz, 1H, H-3), 4.95 (d, J = 10.6 Hz, 1H, CH 2 Ar), 4.90 (d, J = 11.1 Hz, 1H, CH 2 Ar), (m, 4H, CH 2 Ar), (m, 4H, CH 2 Ar), 4.67 (d, J = 11.0 Hz, 1H, CH 2 Ar), 4.15 (t, J = 9.7, 1H, H-6), 4.08 (t, J = 9.7 Hz, 1H, H-4), 3.98 (t, J = 2.3 Hz, 1H, H-2), 3.94 (dd, J = 11.7, 2.8 Hz, 1H, H-6'a), (m, 3H, H-3', H-5', H-6'b), (m, 2H, H-5, H-4'), 3.59 (dd, J = 9.4, 2.3 Hz, 1H, H-1), (m, 1H, H-2'), 2.47 (dt, J = 18.3, 3.4 Hz, 1H, CH 2 ), (m, 1H, CH 2 ), 2.01 (t, J = 4.4 Hz, 1H, CH), (m, 2H, CH 2 ), (m, 1H, CH 2 ), (m, 1H, CH 2 ), 1.07 (s, 9H, t-bu), 1.06 (s, 3H, CH 3 ), 0.89 (s, 3H, CH 3 ); 13 C NMR (150 MHz, CDCl 3 ) (C), (C), (C 2), (C), (C), (C), (CH 2), (CH 2), (CH), (CH), (CH), (CH), (CH), (CH 2), (CH), (CH), (CH 2), (CH 2), (CH 2), (CH 2), (CH 2), (CH 2), (CH), (CH), (CH 2), (CH), (CH 2), (CH), (CH), (CH), (CH), (C), 98.3 (CH), 84.0 (CH), 81.5 (CH), 80.2 (CH), 79.1 (CH), 78.8 (CH), 78.1 (CH), 76.8 (CH), 75.8 (CH 2 ), 75.3 (CH 2 2), 75.2 (CH 2 ), 74.8 (CH 2 ), 74.5 (CH 2 ), 73.6 (CH), 72.8 (CH) 67.9 (C), 63.6 (CH), 62.1 (CH 2 ), 49.1 (C), 44.3 (CH), 43.8 (CH 2 ), 26.9 (CH 3 3), 26.6(CH 2 ), 26.3 (CH 2 ), 21.2 (CH 3 ), 19.6 (CH 3 ), 19.3 (C); HRMS (ESI, MNa + ) calcd for C 84 H 88 N 3 12 NaSi , found S4
5 2-NAP p-brbn TBDPS Bn Bn N 3 Bn Bn 10 NaH EtH/CH 2 Cl 2 60 C, 30 min 95% 2-NAP p-brbn TBDPS Bn Bn N 3 Bn Bn H [2-Azido-3--(4-bromobenzyl)-6--tert-butyldiphenylsilyl-2-deoxy-4--(2- naphthylmethyl)- -D-glucopyranosyl]-2,4,5,6-tetra--benzyl-D-myo-inositol (11). Sodium hydroxide (54 mg, mmol) was added to a solution of compound 10 (98 mg, mmol) in a mixed EtH (4 ml) and CH 2 Cl 2 (1 ml) at room temperature. The mixture was stirred at 60 C for 30 min, and the reaction solution was concentrated in vacuo, and extracted with ethyl acetate (3 20 ml). The combined organic layer was dried over anhydrous MgS 4, filtered, and concentrated in vacuo. Purification of this residue via flash column chromatography (ethyl acetate/hexanes = 1/3) on silica gel gave compound 11 (82 mg, 95%). The water layer was acidified with 6 M H 2 S 4 to ph 2, extracted with ethyl acetate (3 10 ml), and dried over anhydrous MgS 4, filtered, and concentrated in vacuo to recover (1S)-ketopinic acid (11 mg, 88%). [ ] 28 D +5.5 (c 4.2, CHCl 3 ); IR (CHCl 3 ) 3447, 3030, 2929, 2857, 2107, 1454 cm 1 ; 1 H NMR (600 MHz, CDCl 3 ) (m, 1H, Ar-H), (m, 2H, Ar-H), (m, 4H, Ar-H), (m, 1H, Ar-H), (m, 2H, Ar-H), (m, 29H, Ar-H), (m, 2H, Ar-H), 5.41 (d, J = 3.7 Hz, 1H, H- 1'), 5.04 (d, J = 10.4 Hz, 1H, CH 2 Ar), 4.98 (d, J = 10.4 Hz, 1H, CH 2 Ar), (m, 5H, CH 2 Ar), (m, 5H, CH 2 Ar), 4.15 (t, J = 2.1 Hz, 1H, H-2), (m, 1H, H-3'), 3.92 (t, J = 9.3 Hz, 1H, H-6), (m, 4H, H6'a, H6'b, H-4, H-5'), (m, 2H, H4', H-1), 3.52 (t, J = 9.3, 1H, H-5), 3.48 (dd, J = 9.7, 2.5 Hz, 1H, H-3), 3.36 (dd, J = 10.4, 3.7 Hz, 1H, H-2'), 1.07 (s, 9H, t-bu); 13 C NMR (150 MHz, CDCl 3 ) (C), (C), (C), (C), (CH 2), (CH 2), (C), (C), (C), (C), (C), (CH), (CH), (CH), (CH), (CH), (CH 2), (CH), (CH), (CH), (CH), (CH), (CH), (CH 2), (CH), (CH), (CH), (CH), (CH), (C), 98.8 (CH), 84.0 (CH), 81.9 (CH), 81.8 (CH), 80.1 (CH), 79.5 (CH), 78.4 (CH), 77.2 (CH), 75.7 (CH 2 ), 75.5 (CH 2 ), 75.4 (CH 2 ), 75.1 (CH 2 ), 75.0 (CH 2 ), 74.5 (CH 2 ), 72.9 (CH), 72.4 (CH), 63.5 (CH), 62.6 (CH 2 ), 26.9 (CH 3 3), 19.2 (C); HRMS (ESI, MNa + ) calcd for C 74 H 76 N 3 10 NaSi , found S5
6 TBDPS 2-NAP p-brbn TBDPS N STol Bn Bn Bn Bn H H 7 NIS, TfH CH 2 Cl 2, 4 Å MS 60 to 20 C, 3 h + 2-NAP p-brbn 2-NAP p-brbn Bn Bn N 3 Bn Bn H 11: 41% TBDPS Bn N 3 Bn 12: 49% H Bn Bn Direct D-glucosaminylation of compound 7. A solution of the donor 5 (119 mg, mmol) and acceptor 7 (50 mg, mmol) in anhydrous dichloromethane (4 ml) containing freshly dried 4 Å molecular sieves (1.69 g) was stirred at room temperature for 30 min under nitrogen atmosphere. Then, NIS (25 mg, mmol) was added and the resultant solution was cooled to 60 C. After stirring for 20 minutes, TfH (40 L, mmol) was added to the mixture, and the solution was gradually warmed up to 20 C for 3 hours. Saturated NaHC 3 (10 ml) and 10% Na 2 S 2 3(aq) (10 ml) were added to quench the reaction, and the mixture was filtered through Celite, and extracted with CH 2 Cl 2 (3 20 ml). The combined organic layer was dried over anhydrous MgS 4, filtered, and concentrated in vacuo. Purification of the residue via flash column chromatography (ethyl acetate/hexanes = 1/3) on silica gel gave compound 11 (48 mg, 41%), together with its regioisomer 12 (58 mg, 49%). 3--[2-Azido-3--(4-bromobenzyl)-6--tert-butyldiphenylsilyl-2-deoxy-4--(2- naphthylmethyl)- -D-glucopyranosyl]-2,4,5,6-tetra--benzyl-D-myo-inositol (12). [ ] 28 D +2.6 (c 4.2, CHCl 3 ); IR (CHCl 3 ) 3456, 3064, 3030, 2929, 2857, 2107, 1454 cm 1 ; 1 H NMR (600 MHz, CDCl 3 ) (m, 1H, Ar-H), (m, 2H, Ar-H), (m, 4H, Ar-H), (m, 1H, Ar-H), (m, 2H, Ar-H), (m, 8H, Ar-H), (m, 20H, Ar-H), (m, 1H, Ar-H), (m, 2H, Ar-H), 5.12 (d, J = 3.6 Hz, 1H, H-1'), 5.01 (d, J = 11.2 Hz, 1H, CH 2 Ar), (m, 2H, CH 2 Ar), (m, 2H, CH 2 Ar), (m, 7H, CH 2 Ar), 4.15 (t, J = 2.1 Hz, 1H, H-2), (m, 3H, H-6, H- 5', H-3'), 3.88 (t, J = 9.5, 1H, H-4), (m, 3H, H-6'a, H-6'b, H-5), 3.67 (dd, J = 10.0, 2.1 Hz, 1H, H-4'), 3.49 (dd, J = 9.8, 2.1 Hz, 1H, H-1), (m, 2H, H-2', H-3), 2.28 (brs, 1H, 1-H), (s, 9H, t-bu); 13 C NMR (150 MHz, CDCl 3 ) (C), (C), (C), (C), (CH 2), (CH 2), (C), (C), (C), (C), (CH), (CH), (CH), (CH), (CH 2), (CH), (CH), (CH 2), (CH), (CH), (CH), (CH), (CH), S6
7 126.1 (CH), (CH), (CH), (CH), (C), 93.7 (CH), 83.8 (CH), 81.5 (CH), 80.7 (CH), 80.1 (CH), 78.4 (CH), 76.0 (CH 2 ), 75.6 (CH 2 ), 75.3 (CH 2 ), 75.0 (CH 2 ), 74.8 (CH), 74.7 (CH 2 ), 74.5 (CH 2 ), 74.3 (CH), 72.5 (CH), 71.9 (CH), 63.4 (CH), 62.4 (CH 2 ), 26.9 (CH 3 3), 19.3 (C); HRMS (ESI, MNa + ) calcd for C 74 H 76 N 3 10 NaSi , found NAP p-brbn TBDPS Bn Bn N 3 Bn N 3 H 11 TBAF 95% 2-NAP p-brbn H Bn Bn N 3 H Bn H S1 1--[2-Azido-3--(4-bromobenzyl)-2-deoxy-4--(2-naphthylmethyl)- -Dglucopyranosyl]-2,4,5,6-tetra--benzyl-D-myo-inositol (S1). Tetra-n-butylammonium fluoride (TBAF, 1 M solution in THF, ml, mmol) was added to a mixture of compound 11 (78 mg, mmol) in THF (1 ml) at room temperature. After stirring for 24 hours, water (5 ml) was added to the mixture followed by extraction with ethyl acetate (3 10 ml), and the combined organic layer was washed with brine, dried over anhydrous MgS 4, filtered, and concentrated in vacuo. Purification of the residue via flash column chromatography (ethyl acetate/hexanes = 1/1) on silica gel furnished the desired diol S1 (60 mg, 95%). [ ] 28 D +9.7 (c 9.4, CHCl 3 ); IR (CHCl 3 ) 3444, 3030, 2922, 2875, 2107, 1454 cm 1 ; 1 H NMR (600 MHz, CDCl 3 ) (m, 3H, Ar-H), (m, 1H, Ar-H), (m, 2H, Ar-H), (m, 2H, Ar-H), (m, 7H, Ar-H), (m, 14H, Ar-H), (m, 2H, Ar-H), 5.51 (d, J = 3.4 Hz, 1H, H-1'), 5.13 (d, J = 10.6 Hz, 1H, CH 2 Ar), 5.09 (d, J = 10.6 Hz, 1H, CH 2 Ar), 5.06 (d, J = 11.5 Hz, 1H, CH 2 Ar), (m, 4H, CH 2 Ar), (m, 2H, CH 2 Ar), (m, 3H, CH 2 Ar), 4.27 (t, J = 9.5 Hz, 1H, H-6), (m, 2H, H-2, H-3'), 3.96 (t, J = 9.5, 1H, H-4), (m, 3H, H-5', H-6'a, H-1), 3.79 (dd, J = 11.9, 3.5 Hz, 1H, H-6'b), 3.74 (t, J = 9.1 Hz, 1H, H-4'), 3.69 (dd, J = 9.7, 2.3 Hz, 1H, H-3), 3.62 (t, J = 9.2 Hz, 1H, H-5), 3.37 (dd, J = 10.3, 3.4 Hz, 1H, H-2'), 2.34 (brs, 2H, H); 13 C NMR (150 MHz, CDCl 3 ) (C), (C), (C), (C), (C), (C), (C), (C), (CH 2), (CH 2), (CH 2), (CH 2), (CH 2), (CH 2), (CH), (CH 2), (CH), (CH 2), (CH), (CH), (CH 2), (CH), (CH), (CH 2), (CH), (CH), (CH), (CH), (C), 98.7 (CH), 83.9 (CH), 81.7 (CH), 81.6 (CH), 79.7 (CH), 79.5 (CH), 77.9 (CH), 77.0 (CH), 75.6 (CH 2 ), 75.4 (CH 2 ), 75.3 (CH 2 ), (CH 2 ), (CH 2 ), 74.3 (CH 2 ), 72.4 (CH), 72.2 S7
8 (CH), 63.2 (CH), 61.2 (CH 2 ); HRMS (ESI, MNa + ) calcd for C 58 H 58 N 3 10 Na , found NAP p-brbn H Bn Bn Pd(H) 2, H 2, HCl (aq) N 3 Bn Bn H MeH, 98% S1 H H HCl H H 2 N H 4 H H H H 1--(2-amino-2-deoxy- -D-glucopyranosyl)-D-myo-inositol hydrochloride (4). A solution of compound S1 (89 mg, mmol) and 20% Pd(H) 2 (536 mg) in a mixed MeH (3 ml), H 2 (0.5 ml) and 0.1 N of HCl aq (0.1 ml) was purged 3 times with a balloon filled with hydrogen gas, and then stirred under hydrogen balloon for 3 days. The reaction was then filtered through Celite, and the filtrate was concentrated in vacuo. After concentration and desalting through a Sephadex G-10 column eluted with water, the collected fraction was concentrated to afford the pseudodisaccharide 4 (32 mg, 98%) as a colorless oil. [ ] 28 D (c 1.6, H 2 ); 1 H NMR (600 MHz, D 2 ) 5.37 (d, J = 3.7 Hz, 1H, H-1'), 4.15 (t, J = 2.5 Hz, 1H, H-2), (m, 1H, H-3'), (m, 2H, H-6'a, H-5'), (m, 2H, H-6'b, H-6), 3.65 (dd, J = 10.1, 2.7 Hz, 1H, H-1), 3.57 (t, J = 9.5 Hz, 1H, H-4), 3.50 (dd, J = 10.0, 2.6 Hz, 1H, H-3), 3.45 (t, J = 9.5 Hz, 1H, H-4'), 3.31 (dd, J = 10.7, 3.7 Hz, 1H, H- 2'), 3.26 (t, J = 9.4 Hz, 1H, H-5); 13 C NMR (150 MHz, D 2 ) 97.3 (CH), 78.9 (CH), 74.1 (CH), 72.7 (CH), 72.0 (CH), 71.9 (CH), 71.7 (CH), 70.9 (CH), 69.6 (CH), 69.4 (CH), 60.3 (CH 2 ), 54.3 (CH); HRMS (ESI, MH + ) calcd for C 12 H 24 N , found This compound has also been previously characterized. 1,2 H H HCl H H 2 N H 4 H H H H NHBoc SAc H 2 C 13 HATU, DIPEA, DMF, 12 h, 78% H H AcS H H HN NHBoc 14 H H H H 1--[2-deoxy-2-(N-tert-butyloxycarbonyl-S-acetyl-L-cysteinyl)amino- -Dglucopyranosyl]-D-myo-inositol (14). To a solution of 4 (21 mg, mmol) and 13 (29 mg, mmol) in anhydrous N,N-dimethylformamide (DMF, 2 ml) was added -(7- azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluorophosphate (HATU, 42 mg, mmol) and diisopropylethylamine (DIPEA, 29 μl, mmol) at 4 C under nitrogen atmosphere. After stirring for 12 hours at room temperature, the reaction was concentrated in vacuo. Purification of the residue via flash column chromatography (CH 2 Cl 2 /methanol/acetic S8
9 acid = 80/20/1) on silica gel gave compound 14 (26 mg, 78%). [ ] 27 D +9.3 (c 1.0, H 2 ); 1 H NMR (600 MHz, D 2 ) 5.12 (d, J = 4.4 Hz, 1H), 4.31 (dd, J = 8.2, 4.7 Hz, 1H), (brs, 1H), 3.94 (dd, J = 10.7, 3.4 Hz, 1H), (m, 3H), (m, 2H), 3.60 (t, J = 9.6 Hz, 1H), 3.57 (dd, J = 10.3, 2.5 Hz, 1H), 3.52 (dd, J = 9.9, 2.6 Hz, 1H), 3.46 (t, J = 9.5 Hz, 1H), 3.39 (dd, J = 14.2, 4.7 Hz, 1H), 3.25 (t, J = 9.4 Hz, 1H), 3.11 (dd, J = 14.2, 8.6 Hz, 1H), 2.38 (s, 3H), 1.42 (s, 9H); 13 C NMR (150 MHz, D 2 ) (C), (C), (C), 99.1 (CH), 81.9 (C), 79.0 (CH), 74.2 (CH), 72.5 (CH), 72.1 (CH 2), 71.7 (CH), 71.0 (CH), 70.7 (CH), 70.0 (CH), 60.5 (CH 2 ), 54.1 (CH), 54.0 (CH), 30.7 (CH 2 ), 29.8 (CH 3 ), 27.5 (CH 3 3); HRMS (ESI, MNa + ) calcd for C 22 H 38 N 2 14 SNa , found This compound has also been previously characterized. 2 H H H H H H HN H H 1. TFA 2. pyridine H H H H H H HN H H NHAc AcS NHBoc 14 HS 1 1--[2-deoxy-2-(N-acetyl-L-cysteinyl)amino- -D-glucopyranosyl]-D-myo-inositol (1). Cold trifluoroacetic acid (TFA, 0.4 ml) was added to compound 14 (5.3 mg, mmol) and the mixture was stirred for 20 minutes at 4 C. The reaction was, then, concentrated in vacuo, and pyridine (0.6 ml) was added to the residue. After stirred for 30 minutes at room temperature, the reaction was concentrated in vacuo and azeotroped with water and toluene to obtain compound 1 (4.4 mg, 100%). [ ] 27 D (c 0.5, H 2 ); 1 H NMR (600 MHz, D 2 ) 5.12 (d, J = 3.6 Hz, 1H), 4.51 (t, J = 6.1 Hz, 1H), 4.18 (t, J = 2.5 Hz, 1H), 3.97 (dd, J = 10.7, 3.7 Hz, 1H), (m, 2H), (m, 3H), 3.62 (t, J = 9.5 Hz, 1H), 3.57 (dd, J = 10.1, 2.8 Hz, 1H), 3.51 (dd, J = 9.9, 2.8 Hz, 1H), 3.46 (t, J = 9.5 Hz, 1H), 3.28 (t, J = 9.5 Hz, 1H), 2.92 (dd, J = 14.3, 5.3 Hz, 1H), 2.88 (dd, J = 14.3, 7.2 Hz, 1H), 2.05 (s, 3H); 13 C NMR (150 MHz, D 2 ) (C), (C), 99.2 (CH), 79.0 (CH), 74.2 (CH), 72.5 (CH), 72.1 (CH), 72.0 (CH), 71.7 (CH), 71.0 (CH), 70.8 (CH), 70.0 (CH), 60.5 (CH 2 ), 55.7 (CH), 53.8 (CH), 25.6 (CH 2 ), 21.7 (CH 3 ); HRMS (ESI, MNa + ) calcd for C 17 H 30 N 2 12 NaS , found This compound has also been previously characterized. 2,3 References: (1) Jardine, M. A.; Spies, H. S. C.; Nkambule, C. M.; Gammon, D. W.; Steenkamp, D. J. Bioorg. Med. Chem. 2002, 10, (2) Ajayi, K.; Thakur, V. V.; Lapo, R. C.; Knapp, S. rg. Lett. 2010, 12, (3) Lee, S.; Rosazza, J. P. N. rg. Lett. 2004, 6, S9
10 Bn H Bn Bn Bn NAME CC EXPN 1 PRCN 1 Date_ Time PRBHD 5 mm CPTCI 1H- PULPRG zg TD SLVENT CDCl3 NS 20 SWH Hz FIDRES Hz AQ sec RG 9 DW usec TD0 1 NUC1 1H P usec PL db PL1W W SF MHz SI SF MHz LB 0 Hz ppm S10
11 NAME CC EXPN 2 PRCN 1 Bn H Bn Bn Bn Date_ Time 0.11 PRBHD 5 mm CPTCI 1H- PULPRG zgpg30 TD SLVENT CDCl3 NS 3000 SWH Hz FIDRES Hz AQ sec RG 2050 DW usec D sec TD0 3 NUC1 13C P usec PL db PL1W W SF MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db PL db PL2W W PL12W W PL13W W SF MHz SI SF MHz LB 3.00 Hz ppm S11
12 Bn Bn Bn Bn H NAME CCC-80-5 EXPN 1 PRCN 1 Date_ Time PRBHD 5 mm CPTCI 1H- PULPRG zg TD SLVENT CDCl3 NS 20 SWH Hz FIDRES Hz AQ sec RG 6.35 DW usec TD0 1 NUC1 1H P usec PL db PL1W W SF MHz SI SF MHz LB 0 Hz ppm S12
13 NAME CCC-80-5 EXPN 7 PRCN 1 Bn Bn Bn Bn H Date_ Time 5.25 PRBHD 5 mm CPTCI 1H- PULPRG zgpg30 TD SLVENT CDCl3 NS 5000 SWH Hz FIDRES Hz AQ sec RG 2050 DW usec D sec TD0 5 NUC1 13C P usec PL db PL1W W SF MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db PL db PL2W W PL12W W PL13W W SF MHz SI SF MHz LB 3.00 Hz ppm S13
14 Bn Bn Bn Bn NAME CCC-80-1 EXPN 1 PRCN 1 Date_ Time 9.53 PRBHD 5 mm CPTCI 1H- PULPRG zg TD SLVENT CDCl3 NS 16 SWH Hz FIDRES Hz AQ sec RG 2.56 DW usec TD0 1 NUC1 1H P usec PL db PL1W W SF MHz SI SF MHz LB 0 Hz ppm S14
15 NAME CCC-80-1 EXPN 7 PRCN 1 Bn Bn Bn Bn Date_ Time 3.38 PRBHD 5 mm CPTCI 1H- PULPRG zgpg30 TD SLVENT CDCl3 NS 2000 SWH Hz FIDRES Hz AQ sec RG 2050 DW usec D sec TD0 2 NUC1 13C P usec PL db PL1W W SF MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db PL db PL2W W PL12W W PL13W W SF MHz SI SF MHz LB 3.00 Hz ppm S15
16 NAME CC-87 EXPN 1 PRCN 1 2-NAP PBB TBDPS Bn Bn N 3 Bn Bn Date_ Time PRBHD 5 mm CPTCI 1H- PULPRG zg TD SLVENT CDCl3 NS 20 SWH Hz FIDRES Hz AQ sec RG 9 DW usec TD0 1 NUC1 1H P usec PL db PL1W W SF MHz SI SF MHz LB 0 Hz ppm S16
17 NAME CC-87 EXPN 2 PRCN 1 2-NAP p-brbn TBDPS Bn Bn N 3 Bn Bn Date_ Time 5.56 PRBHD 5 mm CPTCI 1H- PULPRG zgpg30 TD SLVENT CDCl3 NS 5100 SWH Hz FIDRES Hz AQ sec RG 2050 DW usec D sec TD0 6 NUC1 13C P usec PL db PL1W W SF MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db PL db PL2W W PL12W W PL13W W SF MHz SI SF MHz LB 3.00 Hz ppm S17
18 NAME CCC-89 EXPN 1 PRCN 1 2-NAP PBB TBDPS N 3 Bn Bn Bn Bn H Date_ Time 9.46 PRBHD 5 mm CPTCI 1H- PULPRG zg TD SLVENT CDCl3 NS 20 SWH Hz FIDRES Hz AQ sec RG 7.12 DW usec TD0 1 NUC1 1H P usec PL db PL1W W SF MHz SI SF MHz LB 0 Hz ppm S18
19 NAME CCC-89 EXPN 7 PRCN 1 2-NAP PBB TBDPS N 3 Bn Bn Bn Bn H Date_ Time PRBHD 5 mm CPTCI 1H- PULPRG zgpg30 TD SLVENT CDCl3 NS 3000 SWH Hz FIDRES Hz AQ sec RG 2050 DW usec D sec TD0 3 NUC1 13C P usec PL db PL1W W SF MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db PL db PL2W W PL12W W PL13W W SF MHz SI SF MHz LB 3.00 Hz ppm S19
20 NAME CCC-71 EXPN 1 PRCN 1 2-NAP p-brbn TBDPS Bn H N 3 Bn Bn Bn Date_ Time PRBHD 5 mm CPDCH 13C PULPRG zg30 TD SLVENT CDCl3 NS 30 SWH Hz FIDRES Hz AQ sec RG 36 DW usec TD0 1 NUC1 1H P usec PL db PL1W W SF MHz SI SF MHz LB 0 Hz ppm S20
21 NAME CCC-71 EXPN 2 PRCN 1 2-NAP p-brbn TBDPS Bn H N 3 Bn Bn Bn Date_ Time PRBHD 5 mm CPDCH 13C PULPRG zgpg30 TD SLVENT CDCl3 NS 55 SWH Hz FIDRES Hz AQ sec RG 3640 DW usec DE 6.00 usec D sec TD0 1 NUC1 13C P usec PL db PL1W W SF MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db PL db PL2W W PL12W W PL13W W SF MHz SI SF MHz LB 2.00 Hz ppm S21
22 NAP PBB H N 3 Bn Bn Bn Bn H NAME CCC-141 EXPN 1 PRCN 1 Date_ Time PRBHD 5 mm CPTCI 1H- PULPRG zg TD SLVENT CDCl3 NS 16 SWH Hz FIDRES Hz AQ sec RG 3.2 DW usec TD0 1 NUC1 1H P usec PL db PL1W W SF MHz SI SF MHz LB 0 Hz ppm S22
23 NAME CCC-141 EXPN 7 PRCN 1 2-NAP PBB H N 3 Bn Bn Bn Bn H Date_ Time PRBHD 5 mm CPTCI 1H- PULPRG zgpg30 TD SLVENT CDCl3 NS 1600 SWH Hz FIDRES Hz AQ sec RG 2050 DW usec D sec TD0 1 NUC1 13C P usec PL db PL1W W SF MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db PL db PL2W W PL12W W PL13W W SF MHz SI SF MHz LB 3.00 Hz ppm S23
24 H NAME CCC-101 EXPN 1 PRCN 1 Date_ Time PRBHD 5 mm CPTCI 1H- PULPRG zg TD SLVENT D2 NS 8 SWH Hz FIDRES Hz AQ sec RG 1 DW usec TE K TD0 1 NUC1 1H P usec PL db PL1W W SF MHz SI SF MHz LB 0.30 Hz ppm H H HCl. NH 2 H H H H H S24
25 H H NAME CCC-101 EXPN 7 PRCN 1 H HCl. NH 2 H H H H H Date_ Time PRBHD 5 mm CPTCI 1H- PULPRG zgpg30 TD SLVENT D2 NS 2000 SWH Hz FIDRES Hz AQ sec RG 2050 DW usec D sec TD0 2 NUC1 13C P usec PL db PL1W W SF MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db PL db PL2W W PL12W W PL13W W SF MHz SI SF MHz LB 3.00 Hz ppm S25
26 H H H HN AcS NHBoc H H H H H NAME CCC EXPN 1 PRCN 1 Date_ Time PRBHD 5 mm CPDCH 13C PULPRG zg30 TD SLVENT D2 NS 18 SWH Hz FIDRES Hz AQ sec RG 36 DW usec TD0 1 NUC1 1H P usec PL db PL1W W SF MHz SI SF MHz LB 0 Hz ppm S26
27 NAME CCC-208-P-All EXPN 2 PRCN 1 H H H HN AcS NHBoc H H H H H Date_ Time PRBHD 5 mm CPDCH 13C PULPRG zgpg30 TD SLVENT D2 NS 4800 SWH Hz FIDRES Hz AQ sec RG 3640 DW usec D sec TD0 1 NUC1 13C P usec PL db PL1W W SF MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db PL db PL2W W PL12W W PL13W W SF MHz SI SF MHz LB 2.00 Hz ppm S27
28 NAME CCC-212 EXPN 1 PRCN 1 H Date_ Time PRBHD 5 mm CPDCH 13C PULPRG zg30 TD SLVENT D2 NS 65 SWH Hz FIDRES Hz AQ sec RG 36 DW usec TD0 1 H H H H H H H HN HS NHAc NUC1 1H P usec PL db PL1W W SF MHz S28 SI SF MHz LB 0 Hz ppm
29 NAME CCC-212-P-All EXPN 2 PRCN 1 H H H HN HS NHAc H H H H H Date_ Time PRBHD 5 mm CPDCH 13C PULPRG zgpg30 TD SLVENT D2 NS 5352 SWH Hz FIDRES Hz AQ sec RG 3640 DW usec D sec TD0 1 NUC1 13C P usec PL db PL1W W SF MHz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db PL db PL2W W PL12W W PL13W W SF MHz SI SF MHz LB 2.00 Hz ppm S29
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