Supplementary Information. Catalytic reductive cleavage of methyl -D-glucoside acetals to ethers using hydrogen as a clean reductant
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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 24 Supplementary Information Catalytic reductive cleavage of methyl -D-glucoside acetals to ethers using hydrogen as a clean reductant Charlotte Gozlan, a,b Romain Lafon, a Nicolas Duguet, a Andreas Redl b and Marc Lemaire *,a a Laboratoire de CAtalyse SYnthèse et ENvironnement (CASYEN), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), CNRS, UMR-5246, Université Claude Bernard Lyon, 43 boulevard du novembre 98, Bât. Curien/CPE, 69622, Villeurbanne, France. marc.lemaire.chimie@univ-lyon.fr ; Fax: ; Tel: b TERES SYRAL SAS, Z.I et Portuaire B.P.32, 6739 Marckolsheim, France. andreas.redl@tereos.com ; Tel: Table of contents. General information Derivatization method GC method General procedures Characterization data Characterization data of methyl -D-glucoside acetals 2a-e Characterization data of methyl -D-glucoside ethers 3a-e and 4a-e H and 3 C NMR spectra H and 3 C spectra of methyl -D-glucoside acetals 2a-e H and 3 C spectra of methyl -D-glucoside ethers 3a-e and 4a-e...4
2 . General information Methyl -D-glucoside (> 98% purity) was purchased from Sigma-Aldrich or Alfa-Aesar and Pd/C (5 or %, Pd on activated carbon, reduced and dry, Escat 43) from Strem Chemicals. Valeraldehyde, hexanal, octanal, decanal and dodecanal were supplied by Sigma-Aldrich or Alfa- Aesar. Amberlyst 5 dry was bought from Rohm and Haas. All other reagents and solvents were used as received without further purification. NMR spectra were acquired on a Bruker 3 ( H, 3 MHz; 3 C, 75 MHz) spectrometer at 293 K. Shifts are referenced relative to the CDCl 3 residual peak (δ H : 7.26 ppm; δ C : 77.6 ppm). The chemical shifts (δ) are expressed in ppm and the coupling constants (J) are given in Hz. The following abbreviations used are: s = singlet, d = doublet, t = triplet, dd = doublet of doublets, td = triplet of doublets, m = multiplet, br = broad. Electrospray ionization (ESI) mass spectra (MS) and High-Resolution Mass Spectra (HRMS) were recorded in the positive mode using spectrometer (MicroTFQ-II, Bruker Daltonics, Bremen). Thin-layer chromatography (TLC) was carried out on aluminum sheets coated with silica gel Merck 6 F254 (.25 mm) revealed with a solution of sulfuric acid at v/v% in ethanol. Flash column chromatography was performed with silica gel Merck Si 6 (4 63 μm). Infrared (IR) spectra were recorded in a SMART itr-nicolet is spectrometer using Attenuated Total Reflectance (ATR) and the wavenumbers ( max) are expressed in cm -. Melting points were measured using a Kofler apparatus and noted in C. 2. Derivatization method Prior to analysis, the sample was silylated as follows: the crude mixture was diluted in THF (25mL), then ml of this solution was diluted in.3 ml of the silylating reagent (pyridine:hexamethyldisilazane (HMDS):chlorotrimethylsilane (TMSCl) in v/v/v :.2:. proportions) The mixture was then heated at 7 C and stirred vigorously for min. Then, the sample was diluted in ml of a THF solution containing methyl oleate (internal standard) at.3 g/l. Finally, the sample was filtrated using a syringe filter (PTFE;.2 µm) before injection in GC. 3. GC method Gas chromatography analyses (GC) for the optimization of the hydrogenolysis of methyl -Dglucoside acetals were performed using a Shimadzu GC (GC-225) equipped with a DB-5MS capillary column (3 m,.25 mm i.d,.25 µm film thickness) and a FID as detector. The carrier gas was helium, at a flow rate of.24 ml/min. The column temperature was initially at C, gradually increased to 24 C at 8 C/min and kept at 24 C for 3 min., then gradually increased to 28 C at 8 C/min. and finally kept at 28 C for min. The injector temperature was set at 24 C and the transfer line temperature was at 28 C. C.C. Sweeley, R. Bentley, M. Makita, W.W. Wells, J. Am. Chem. Soc., 963, 85,
3 4. General procedures General procedure for the preparation of methyl α-d-glucoside acetals (A) In a -ml round bottom flask, under an argon atmosphere, methyl -D-glucoside (3.22 g, 6.6 mmol, 2 equiv) was dissolved in dry THF ( ml) with sodium sulfate (.8 g, 2 mmol,.5 equiv) under an argon atmosphere. The aldehyde (8.3 mmol, equiv) was added dropwise over a -min period, followed by Amberlyst 5 (2wt%/aldehyde). The mixture was magnetically stirred at reflux (66 C) for 3 hours. After cooling to room temperature, the reaction mixture was filtered, washed with EtAc (2 25 ml) and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (EtAc:cylohexane) to give methyl 4,6--alkylidene -D-glucoside 2a-e as a single diastereoisomer. General procedure for the reductive cleavage of methyl α-d-glucoside acetals (B) Methyl 4,6--alkylidene -D-glucoside 2a-e (3 mmol) was diluted in dry CPME (3 ml) and 5%- Pd/C (.45 g, 5 mol% in Pd) was added in a -ml stainless steel autoclave. The reactor was tightly closed, purged three times with hydrogen and hydrogen pressure was introduced (3 bar). The system was heated at 2 C and mechanically stirred for 5 hours. After cooling to room temperature, hydrogen pressure was released and the reaction mixture was then dissolved in absolute ethanol ( ml) and filtered (Millipore Durapore filter. µm). The filtrate was evaporated under reduced pressure and the residue was purified by flash chromatography (EtAc/cyclohexane 5:5 to : then EtH/EtAc :9) to give methyl glucoside ethers 3a-e and 4a-e as a colourless oil. GC analysis after silylation revealed a mixture of 4-and 6-ether regioisomers. 5. Characterization data 5.. Characterization data of methyl -D-glucoside acetals 2a-e H a H Me Methyl 4,6--pentylidene -D-glucopyranoside [ ] (2a): The title compound was prepared from methyl -D-glucoside (7.49 g, 3 mmol) and valeraldehyde (.64 g, 9 mmol) following the procedure A to give 2a (2.4 g, 43%) as a white solid. Mp = 78 C; H NMR (3 MHz, CDCl 3 ) δ H :.88 (3H, t, J = 7, CH 3 alkyl),.2.44 (4H, m, 2(CH 2 ) alkyl), (2H, m, CH 2 alkyl), 2.8 (H, d, J = 9, H 3 ), 3.23 (H, t, J = 9, H 3 ), 3.3 (H, d, J=2, H 2 ), 3.4 (3H, s, CH 3 ), 3.48 (H, t, J=, H 2 ), (2H, m, H 5 +H 6 ), 3.83 (H, td, J=9 and 2, H 4 ), 4.9 (H, dd, J= and 4, H 6 ), 2 (H, t, J=5, H 7 ), 4.73 (H, d, J=4, H ); 3 C NMR (75 MHz, CDCl 3 ) δ C : (CH 3 alkyl), (CH 2 alkyl), 26.3 (CH 2 alkyl), 34.3 (CH 2 alkyl), 54 (CH 3 ), (CH 5 ), 67 (CH 26 ), 7.7 (CH 4 ), (CH 2 ), 8.47 (CH 3 ), (CH ), 2.8 (CH 7 ). IR ν max : 3399 (H), 2956 (-CH 3 ), 2862 (-CH 2 -), 428, 39, 62, 4, 989; HRMS (ESI + ) calcd for C 2 H 22 Na 6 : [M+Na] +,found: (-2.2 ppm); GC: R t = 5.85 min; Rf =.27 (8:2 EtAc/cyclohexane). 3
4 H b H Me Methyl 4,6--hexylidene -D-glucopyranoside [ ] (2b): The title compound was prepared from methyl -D-glucoside (3.22 g, 6.6 mmol) and hexanal (.83 g, 8.3 mmol) following the procedure A to give 2b (.98 g, 43%) as a white solid. Mp = 84 C; H NMR (3 MHz, CDCl 3 ) δ H :.86 (3H, t, J = 7, CH 3 alkyl),.5.3 (4H, m, 2(CH 2 ) alkyl),.3.46 (2H, m, CH 2 alkyl), (2H, m, CH 2 alkyl), 3.2 (H, br s, H 3 ), 3.23 (H, t, J = 9, H 3 ), 3.4 (3H, s, CH 3 ), 3.47 (H, t, J=, H 2 ), (2H, m, H 5 +H 6 ), 3.83 (H, t, J=9, H 4 ), 4.9 (H, dd, J= and 5, H 6 ), 2 (H, t, J=5, H 7 ), 4.72 (H, d, J=4, H ); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4. (CH 3 alkyl), (CH 2 alkyl), (CH 2 alkyl), 3.74 (CH 2 alkyl), (CH 2 alkyl), 5 (CH 3 ), (CH 5 ), 66 (CH 26 ), 7.6 (CH 4 ), (CH 2 ), 8.49 (CH 3 ), 99.9 (CH ), 2.8 (CH 7 ); IR ν max : 3433 (H), 2925 (-CH 3 ), 286 (-CH 2 -), 465, 379, 6, 983; HRMS (ESI + ) calcd for C 3 H 24 Na 6 : [M+Na] + ; found: (+.4 ppm); GC: R t = 7.37 min; Rf =.27 (8:2 EtAc/cyclohexane). H c H Me Methyl 4,6--octylidene -D-glucopyranoside [ ] (2c): The title compound was prepared from methyl -D-glucoside (3.22 g, 6.6 mmol) and octanal (.6 g, 8.3 mmol) following the procedure A to give 2c (.94 g, 37%) as a white solid. Mp = 8 C; H NMR (3 MHz, CDCl 3 ) δ H :.85 (3H, t, J = 7, CH 3 alkyl),.7.3 (8H, m, 4(CH 2 ) alkyl), (2H, m, CH 2 alkyl),.5.73 (2H, m, CH 2 alkyl), 3.2 (2H, br s, H 2 +H 3 ), 3.23 (H, t, J = 9, H 3 ), 3.4 (3H, s, CH 3 ), 3.48 (H, t, J=, H 2 ), (2H, m, H 5 ), 3.83 (H, t, J=9, H 4 ), 4.9 (H, dd, J= and 5, H 6 ), 2 (H, t, J=5, H 7 ), 4.72 (H, d, J=4, H ); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.8 (CH 3 alkyl), (CH 2 alkyl), 24.8 (CH 2 alkyl), (CH 2 alkyl), 2 (CH 2 alkyl), 3.85 (CH 2 alkyl), (CH 2 alkyl), 53 (CH 3 ), (CH 5 ), 66 (CH 26 ), 7.68 (CH 4 ), (CH 2 ), 8.48 (CH 3 ), (CH ), 2.82 (CH 7 ); IR ν max : 3368 (H), 2924 (-CH 3 ), 2857 (-CH 2 -), 465, 378, 28, 9, 64, 37, 993; HRMS (ESI + ) calcd for C 5 H 28 Na 6 : [M+Na] + ; found: (-.6 ppm); GC: R t = 9.86 min; Rf =.2 (5:5 EtAc/cyclohexane). H d H Me Methyl 4,6--decylidene -D-glucopyranoside [ ] (2d): The title compound was prepared from methyl -D-glucoside (2 g, 2 mmol) and decanal (7.97 g, 5 mmol) following the procedure A to give 2d (7.48 g, 44%) as a white solid. Mp = 72 C; H NMR (3 MHz, CDCl 3 ) δ H :.87 (3H, t, J = 7, CH 3 alkyl),.6.32 (2H, m, 6(CH 2 ) alkyl), (2H, m, CH 2 alkyl), (2H, m, CH 2 alkyl), 2.6 (2H, br s, H 3 +H 2 ), 3.24 (H, t, J = 9, H 3 ), 3.42 (3H, s, CH 3 ), 3.49 (H, t, J=, H 2 ), (2H, m, H 5 ), 3.84 (H, t, J=9, H 4 ), 4. (H, dd, J= and 5, H 6 ), 3 (H, t, J=5, H 7 ), 4.74 (H, d, J=4, H ); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.3 (CH 3 alkyl), 29 (CH 2 alkyl), 24.8 (CH 2 alkyl), (CH 2 alkyl), (CH 2 alkyl), (2CH 2 alkyl), 3.82 (CH 2 alkyl), 34.9 (CH 2 alkyl), 55.2 (CH 3 ), 64 (CH 5 ), (CH 26 ), 7.9 (CH 4 ), (CH 2 ), 3 (CH 3 ),.2 (CH ), 2.64 (CH 7 ); IR ν max : 3393 (H), 2922 (-CH 3 ), 2853 (-CH 2 -), 466, 378, 2, 88, 4
5 63, 37, 99; HRMS (ESI + ) calcd for C 7 H 32 Na 6 : [M+Na] + ; found: (-3.2 ppm); GC: R t = 2 min; Rf =.32 (8:2 EtAc/cyclohexane). H e H Me Methyl 4,6--dodecylidene -D-glucopyranoside [ ] (2e): The title compound was prepared from methyl -D-glucoside (3.22 g, 6.6 mmol) and dodecanal (.52 g, 8.3 mmol) following the procedure A to give 2e (.77 g, 26%) as a white solid. Mp = 69 C; H NMR (3 MHz, CDCl 3 ) δ H :.86 (3H, t, J = 7, CH 3 alkyl),.7.32 (6H, m, 8(CH 2 ) alkyl), (2H, m, CH 2 alkyl), (2H, m, CH 2 alkyl), 2.85 (2H, br s, H 3 +H 2 ), 3.24 (H, t, J = 9, H 3 ), 3.4 (3H, s, CH 3 ), 3.49 (H, t, J=, H 2 ), (2H, m, H 5 ), 3.84 (H, t, J=9, H 4 ), 4. (H, dd, J= and 5, H 6 ), 2 (H, t, J=5, H 7 ), 4.74 (H, d, J=4, H ); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.24 (CH 3 alkyl), 22.8 (CH 2 alkyl), 24.2 (CH 2 alkyl), (CH 2 alkyl), 28 (CH 2 alkyl), (CH 2 alkyl), (CH 2 alkyl), (CH 2 alkyl), (CH 2 alkyl), 32.3 (CH 2 alkyl), (CH 2 alkyl), 57 (CH 3 ), (CH 5 ), 67 (CH 26 ), 7.8 (CH 4 ), 73.2 (CH 2 ), 8.46 (CH 3 ), (CH ), 2.84 (CH 7 ); IR ν max : 3388 (H), 292 (-CH 3 ), 2852 (-CH 2 -), 466, 378, 89, 63, 37, 99; HRMS (ESI + ) calcd for C 9 H 36 Na 6 : [M+Na] + ; found: (+.6 ppm); GC: R t = min; Rf =.3 (6:4 EtAc/cyclohexane) Characterization data of methyl -D-glucoside ethers 3a-e and 4a-e H H 3a H Me H H 4a H Me Methyl 6--pentyl -D-glucopyranoside (3a) and methyl 4--pentyl -D-glucopyranoside (4a): The title compounds were prepared from methyl -D-glucoside acetal 2a (4. g, 5 mmol) following the procedure B to give a 7:3 mixture of 3a and 4a (.5 g, 38%) as a white paste. The mixture of ethers was purified by column chromatography (EtAc/cyclohexane 5:5 to : then EtH/EtAc :9) for the characterization of each regioisomer. 3a: colourless oil. H NMR (3 MHz, CDCl 3 ) δ H :.84 (3H, t, J = 7, CH 3 alkyl),.4.36 (4H, m, 2(CH 2 ) alkyl),.4.68 (2H, m, CH 2 alkyl), 3.34 (3H, s, CH 3 ), (7H, m), (4H, m, CH-anomeric + 3H); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.6 (CH 3 alkyl), 23 (CH 2 alkyl), 28.2 (CH 2 alkyl), (CH 2 alkyl), 55.2 (CH 3 ), 7.2 (CH 2 ), 7 (CH), 7.74 (CH), 7.9 (CH), 7 (CH 2 ), (CH), 96 (CH-anomeric); IR ν max : 3382 (H), 2929 (-CH 3 ), 286 (-CH 2 -), 455, 363, 92, 44, 8, 4, 9; HRMS (ESI + ) calcd for C 2 H 24 Na 6 : [M+Na] + ; found: (-.8 ppm); GC: R t = 7.64 min; Rf =.35 (: EtAc/EtH). 4a: colourless oil. H NMR (3 MHz, CDCl 3 ) δ H :.86 (3H, t, J = 7, CH 3 alkyl),.6.38 (4H, m, 2(CH 2 ) alkyl), (2H, m, CH 2 alkyl), 3.6 (3H, br s, H), 3.2 (H, t, J = ), 3.37 (3H, s, CH 3 ), (7H, m), 4.7 (H, d, J = 3, CH anomeric); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4. (CH 3 alkyl), 22.6 (CH 2 alkyl), (CH 2 alkyl), (CH 2 alkyl), (CH 3 ), 6.92 (CH 2 ), 7. (CH), 72.6 (CH), 73.4 (CH 2 ), 72 (CH), (CH), (CH-anomeric); IR ν max : 3388 (H), 2928 (-CH 3 ), 2852 (-CH 2 -), 452, 37, 92, 83, 37, 93; HRMS (ESI + ) calcd for C 2 H 24 Na 6 : [M+Na] + ; found: (+.2 ppm); GC: R t = 6.49 min; Rf =.4 (: EtAc/EtH). 5
6 H H 3b H Me H H 4b H Me Methyl 6--hexyl -D-glucopyranoside (3b) and methyl 4--hexyl -D-glucopyranoside (4b): The title compounds were prepared from methyl -D-glucoside acetal 2b ( g, 2 mmol) following the procedure B to give a 72:28 mixture of 3b and 4b (2.8 g, 37%) as a colourless oil. The mixture of ethers was purified by column chromatography (EtAc/cyclohexane 5:5 to : then EtH/EtAc :9) for the characterization of each regioisomer. 3b: colourless oil. H NMR (3 MHz, CDCl 3 ) δ H :.84 (3H, t, J = 7, CH 3 alkyl),.3.38 (6H, m, 3(CH 2 ) alkyl), (2H, m, CH 2 alkyl), 3.38 (3H, s, CH 3 ), (8H, m), 3 (3H, br s, H), 4.7 (H, d, J = 4, CHanomeric); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4. (CH 3 alkyl), (CH 2 alkyl), (CH 2 alkyl), 29.6 (CH 2 alkyl), 3.75 (CH 2 alkyl), 55.8 (CH 3 ), 7.24 (CH 2 ), 5 (CH), 7.79 (CH), 7.94 (CH), 72.3 (CH 2 ), (CH), 96 (CH-anomeric); IR ν max : 3376 (H), 2928 (-CH 3 ), 2859 (-CH 2 - ), 455, 364, 92, 44, 6, 43, 9; HRMS (ESI + ) calcd for C 3 H 26 Na 6 : [M+Na] + ; found: 3.62 (+3.3 ppm); GC: R t = 8.82 min; Rf=.32 (: EtAc/EtH). 4b: colourless oil. H NMR (3 MHz, CDCl 3 ) δ H :.87 (3H, t, J = 7, CH 3 alkyl),.7.4 (6H, m, 3(CH 2 ) alkyl), (2H, m, CH 2 alkyl), (3H, br s, H), 3.23 (H, t, J = ), 3.39 (3H, s, CH 3 ), 3.48 (H, dd, J = and 4), (2H, m), (4H, m), 4.73 (H, d, J = 4, CH-anomeric); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.6 (CH 3 alkyl), (CH 2 alkyl), (CH 2 alkyl), 3.38 (CH 2 alkyl), 3.8 (CH 2 alkyl), 55.4 (CH 3 ), 6 (CH 2 ), 7. (CH), (CH), (CH 2 ), 74.8 (CH), 77.9 (CH), (CH-anomeric); IR ν max : 3395 (H), 2927 (-CH 3 ), 2852 (-CH 2 -), 456, 365, 92, 4, 27, 896; C 3 H 26 Na 6 : [M+Na] + ; found: 3.6 (+4. ppm); GC: R t = 6 min; Rf=.38 (: EtAc/EtH). H H 3c H Me H H 4c H Me Methyl 6--octyl -D-glucopyranoside (3c) and methyl 4--octyl -D-glucopyranoside (4c): The title compounds were prepared from methyl -D-glucoside acetal 2c (5. g, 6.4 mmol) following the procedure B to give a 75:25 mixture of 3c and 4c (2.3 g, 4%) as a colourless oil. The mixture of ethers was purified by column chromatography (EtAc/cyclohexane 5:5 to : then EtH/EtAc :9) for the characterization of each regioisomer. 3c: colourless oil. H NMR (3 MHz, CDCl 3 ) δ H :.86 (3H, t, J = 7, CH 3 alkyl),.5.38 (H, m, 5(CH 2 ) alkyl), (2H, m, CH 2 alkyl), 3.4 (3H, s, CH 3 ), (8H, m), 4.22 (3H, br s, H), 4.73 (H, d, J = 4, CHanomeric); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.22 (CH 3 alkyl), (CH 2 alkyl), 2 (CH 2 alkyl), (CH 2 alkyl), 29 (CH 2 alkyl), (CH 2 alkyl), 3.96 (CH 2 alkyl), 55.3 (CH 3 ), 7.44 (CH 2 ), 7.2 (CH), 72.8 (CH), (CH), (CH 2 ), (CH), 99.6 (CH-anomeric); IR ν max : 337 (H), 2923 (-CH 3 ), 2854 (-CH 2 -), 456, 365, 92, 44, 8, 44, 9; HRMS (ESI + ) calcd for C 5 H 3 Na 6 : [M+Na] + ; found: (- ppm); GC: R t = 2.92 min; Rf =.26 (: EtAc/EtH). 4c: white solid. H NMR (3 MHz, CDCl 3 ) δ H :.86 (3H, t, J = 7, CH 3 alkyl),.9.39 (H, m, 5(CH 2 ) alkyl), (2H, m, CH 2 alkyl), 8 (3H, br s, H), 3.23 (H, t, J = ); 3.39 (3H, s, CH 3 ), 3.48 (H, dd, J = and 4), (2H, m), (4H, m), 4.73 (H, d, J = 4, CH-anomeric); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.2 (CH 3 alkyl), (CH 2 alkyl), 26.8 (CH 2 alkyl), (CH 2 alkyl), 28 (CH 2 alkyl), 3.44 (CH 2 alkyl), 3.93 (CH 2 alkyl), 55.4 (CH 3 ), 62.8 (CH 2 ), 7. (CH), (CH), (CH 2 ), (CH), (CH), (CH-anomeric); IR 6
7 ν max : 3388 (H), 2922 (-CH 3 ), 2853 (-CH 2 -), 456, 365, 92, 44,, 45, 899; C 5 H 3 Na 6 : [M+Na] + ; found: (-.2 ppm); GC: R t = 2.35 min; Rf =.38 (: EtAc/EtH). H H 3d H Me H H 4d H Me Methyl 6--decyl -D-glucopyranoside (3d) and methyl 4--decyl -D-glucopyranoside (4d): (CG478+CG52)The title compounds were prepared from methyl -D-glucoside acetal 2a (6 g, 8 mmol) following the procedure B to give a 77:23 mixture of 3d and 4d (.52 g, 25%) as a white paste. The mixture of ethers was purified by column chromatography (EtAc/cyclohexane 5:5 to : then EtH/EtAc :9) for the characterization of each regioisomer. 3d: colourless oil. H NMR (3 MHz, CDCl 3 ) δ H :.86 (3H, t, J = 7, CH 3 alkyl),..38 (4H, m, 7(CH 2 ) alkyl), (2H, m, CH 2 alkyl), 3.4 (3H, s, CH 3 ), (8H, m), 4.32 (3H, br s, H), 4.73 (H, d, J = 4, CH-anomeric); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.22 (CH 3 alkyl), (CH 2 alkyl), 2 (CH 2 alkyl), (CH 2 alkyl), (CH 2 alkyl), (2CH 2 alkyl), (CH 2 alkyl), 32.2 (CH 2 alkyl), (CH 3 ), 7.4 (CH 2 ), 7.48 (CH), 7.2 (CH), 72.4 (CH), (CH 2 ), 74.4 (CH), 99.6 (CH-anomeric); IR ν max : 34 (H), 299 (-CH 3 ), 2852 (-CH 2 -), 467, 369, 23, 43, 4, 9; HRMS (ESI + ) calcd for C 7 H 34 Na 6 : [M+Na] + ; found: (+. ppm); GC: R t = 2 min; Rf =.3 (: DCM/MeH). 4d: white solid. H NMR (3 MHz, CDCl 3 ) δ H :.88 (3H, t, J = 7, CH 3 alkyl),..39 (4H, m, 7(CH 2 ) alkyl), (2H, m, CH 2 alkyl), 2.3 (4H, br s, H + H), 3.25 (H, t, J = ); 3.4 (3H, s, CH 3 ), 3.48 (H, dd, J = and 4), (2H, m), (3H, m), 4.75 (H, d, J = 4, CH-anomeric); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.25 (CH 3 alkyl), (CH 2 alkyl), 26.2 (CH 2 alkyl), (CH 2 alkyl), (CH 2 alkyl), 29.7 (CH 2 alkyl), (CH 2 alkyl), 3.47 (CH 2 alkyl), 32.2 (CH 2 alkyl), (CH 3 ), 62.8 (CH 2 ), 7.99 (CH), (CH), (CH 2 ), 75.8 (CH), (CH), 99.9 (CH-anomeric); IR ν max : 337 (H), 2923 (-CH 3 ), 2853 (- CH 2 -), 466, 37, 37, 92, 2, 7, 5, 899; C 7 H 34 Na 6 : [M+Na] + ; found: (-.2 ppm); GC: R t = 23.2 min; Rf =.38 (: EtAc/EtH). H H 3e H Me H H 4e H Me Methyl 6--dodecyl -glucopyranoside (3e) and methyl 4--dodecyl -D-glucopyranoside (4e): The title compounds were prepared from methyl -D-glucoside acetal 2e (5. g, 4 mmol) following the procedure B to give a 73:27 mixture of 3e and 4e (2 g, 5%) as a white solid. The mixture of ethers was purified by column chromatography (EtAc/cyclohexane 5:5 to : then EtH/EtAc :9) for the characterization of each regioisomer. 3e: white solid. H NMR (3 MHz, CDCl 3 ) δ H :.87 (3H, t, J = 7, CH 3 alkyl),.9.44 (8H, m, 9(CH 2 ) alkyl),.47.7 (2H, m, CH 2 alkyl), 3.4 (3H, s, CH 3 ), (7H, m), 4.2 (3H, br s, H), 4.74 (H, d, J = 4, CH-anomeric); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.25 (CH 3 alkyl), (CH 2 alkyl), 26.7 (CH 2 alkyl), 2 (CH 2 alkyl), (CH 2 alkyl), (CH 2 alkyl), (CH 2 alkyl), 29.8 (2CH 2 alkyl), (CH 2 alkyl), 32.6 (CH 2 alkyl), (CH 3 ), 7.33 (CH), (CH 2 ), 7.23 (CH), 72. (CH), 72.3 (CH 2 ), (CH), 97 (CH-anomeric); IR ν max : 342 (H), 298 (-CH 3 ), 285 (-CH 2 -), 467, 37, 57, 5, 92; HRMS (ESI + ) calcd for C 9 H 38 Na 6 : [M+Na] + ; found: (+.6 ppm); GC: R t = 26.4 min; Rf =.6 (: EtAc/EtH). 4e: white solid. H NMR (3 MHz, CDCl 3 ) δ H :.87 (3H, t, J = 7, CH 3 alkyl),.4.42 (8H, m, 9(CH 2 ) alkyl),.47.7 (2H, m, CH 2 alkyl), 2.6 7
8 (3H, br s, H), 3.24 (H, t, J = ); 3.4 (3H, s, CH 3 ), 3.49 (H, dd, J = = and 4), (2H, m), (4H, m), 4.74 (H, d, J = 4, CH-anomeric); 3 C NMR (75 MHz, CDCl 3 ) δ C : 4.26 (CH 3 alkyl), (CH 2 alkyl), 26.2 (CH 2 alkyl), (CH 2 alkyl), (CH 2 alkyl), (2CH 2 alkyl), (CH 2 alkyl), 29.8 (CH 2 alkyl), 3.47 (CH 2 alkyl), 32.6 (CH 2 alkyl), (CH 3 ), 6 (CH 2 ), 7.99 (CH), 72.8 (CH), (CH 2 ), 7 (CH), (CH), 99.2 (CH-anomeric); IR ν max : 3295 (H), 293 (-CH 3 ), 2848 (-CH 2 -), 739, 469, 37, 4, 67, 42, 993; C 9 H 38 Na 6 : [M+Na] + ; found: (- ppm); GC: R t = min.; Rf =.24 (: EtAc/EtH). 8
9 6. H and 3 C NMR spectra 6.. H and 3 C spectra of methyl -D-glucoside acetals 2a-e cg492-p Proton E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 4,6--pentylidene -D-glucoside (2a) cg492-p E+8 6E+8 6E+8 5E+8 E f (ppm) 3 C NMR (75 MHz, CDCl 3 ) Methyl 4,6--pentylidene -D-glucoside (2a) 9
10 cg49-p5 Proton E+8 E+8 E+8 8E+7 6E+7 4E+7 2E E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 4,6--hexylidene -D-glucoside (2b) cg49-p E+8 6E+8 6E+8 5E+8 E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 4,6--hexylidene -D-glucoside (2b)
11 cg488-p5 Proton E+8 5E+8 E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 4,6--octylidene -D-glucoside (2c) cg488-p E+8 8E+8 7E+8 6E+8 5E+8 E+8 -E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 4,6--octylidene -D-glucoside (2c)
12 RLCG E+8 5E+8 E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 4,6--decylidene -D-glucoside (2d) RLCG38 RLCG38 R.Lafon CASYEN ML 8mg/CDCl E+8 E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 4,6--decylidene -D-glucoside (2d) 2
13 cg487-p5 Proton E+8 E+8 E+8 8E+7 6E+7 4E+7 2E E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 4,6--dodecylidene -D-glucoside (2e) cg487-p E+9 9E+8 8E+8 7E+8 6E+8 5E+8 E+8 -E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 4,6--dodecylidene -D-glucoside (2e) 3
14 6.2. H and 3 C spectra of methyl -D-glucoside ethers 3a-e and 4a-e ChG59-P3 ChG59-P3 / CASYEN ML E+8 6E+8 6E+8 5E+8 E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 6--pentyl -D-glucoside (3a) ChG59-P3 ChG59-P3 / CASYEN ML E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 6--pentyl -D-glucoside (3a) 4
15 ChG59-P2 ChG59-P2 / CASYEN ML E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 4--pentyl -D-glucoside (4a) ChG59-P2 ChG59-P2 / CASYEN ML E+8 7E+8 6E+8 6E+8 6E+8 5E+8 E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 4--pentyl -D-glucoside (4a) 5
16 ChG58-p4 ChG58-p4 / CASYEN ML E+8 E+8 E+8 8E+7 6E+7 4E+7 2E E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 6--hexyl -D-glucoside (3b) ChG58-p4 ChG58-p4 / CASYEN ML E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 6--hexyl -D-glucoside (3b) 6
17 ChG58-p2 ChG58-p2 / CASYEN ML E E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 4--hexyl -D-glucoside (4b) ChG58-p2 ChG58-p2 / CASYEN ML E+8 E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 4--hexyl -D-glucoside (4b) 7
18 ChG499.6eth ChG499.6eth / Casyen ML E+8 E+8 E+8 8E+7 6E+7 4E+7 2E E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 6--octyl -D-glucoside (3c) ChG499.6eth ChG499.6eth / Casyen ML E+8 E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 6--octyl -D-glucoside (3c) 8
19 ChG499.4eth ChG499.4eth / Casyen ML E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 4--octyl -D-glucoside (4c) ChG499.4eth ChG499.4eth / Casyen ML E+8 E+8 E+8 8E+7 6E+7 4E+7 2E+7-2E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 4--octyl -D-glucoside (4c) 9
20 ChG478.6ethP ChG478.6ethP / CASYEN ML E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 6--decyl -D-glucoside (3d) ChG478.6ethP ChG478.6ethP / CASYEN ML E+8 5E+8 E f (ppm) C NMR(75 MHz, CDCl 3 ) Methyl 6--decyl -D-glucoside (3d) 2
21 cg355-rf Proton E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 4--decyl -D-glucoside (4d) chg355.rf chg355.rf / CASYEN ML E+8 E+8 9E+7 8E+7 7E+7 6E+7 4E+7 3E+7 2E+7 E+7 -E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 4--decyl -D-glucoside (4d) 2
22 ChG49-4P ChG49-4P / CASYEN ML E+8 5E+8 E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 6--dodecyl -D-glucoside (3e) ChG49-4P ChG49-4P / CASYEN ML E+8 E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 6--dodecyl -D-glucoside (3e) 22
23 ChG49-2P ChG49-2P / CASYEN ML E f (ppm) H NMR (3 MHz, CDCl 3 ) Methyl 4--dodecyl -D-glucoside (4e) ChG49-2P ChG49-2P / CASYEN ML E+8 E+8 E+8 8E+7 6E+7 4E+7 2E+7-2E f (ppm) C NMR (75 MHz, CDCl 3 ) Methyl 4--dodecyl -D-glucoside (4e) 23
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