Methyl 6-thio-a-D-glucopyranoside

The reaction of methyl 6-deoxy-6-iodo-2,3,4-tri-0-methyl-a-D-glucopyranoside with methyl 2,3,4-tri-O-methyl-a-D-glucopyranoside 6-0-(S-sodium dithiocarbonate) affords1593 (methyl 2,3,4-tri-O-methyl-6-thio-a-D-glucopyranoside) (methyl 2,3,4-tri-O-methyl-a-D-glucopy-ranoside) 6,6 -dithiocarbonate. 

Following the work of Mclnnes,289,290 methanolysis in the presence of potassium carbonate was used to prepare methyl 6-O-acetyl- and methyl 6-0-octadecanoyl-/3-D-glucopyranoside,291 o-nitrophenyl /3-D-galactopyranoside 6-phosphate,292 methyl 5-thio-a-D-glucopyranoside 6-phosphate,293 and 6,6 -di-0-hexadecanoyl-a,a-trehalose,294 from the appropriate, per-0-(trialkylsilyl)ated precursors. 

Various protected bicyclic 2,5-anhydro derivatives of 5-thio-D-mannitol were obtained from methyl 2,3,4-tri-(9-acetyl-6-(9-mesyl-5-thio-a-D-glucopyranoside by transannular participation of the ring sulfur atom and ring opening of the thiiranium ion [35]. Similar reactions were earlier observed with, for example, a 4-(9-methanesulfony 1-5-thio-D-xylopyranose [36]. 

A soln. of methyl 4,6-0-benzylidene-2-0-mesyl-3-S-phenyl-3-thio-a-D-altropyrano-side refluxed 18 hrs. in dry benzene methyl 4,6-0-benzylidene-3-0-mesyl-2-S-phenyl-2-thio-a-D-glucopyranoside. Y ca. 100. S. Hanessian and A. P. A. Staub. Carbohydrate Res. 14, 424 (1970). 

Me glycoside, 2,3,4-tri-Ac Methyl 2,3,4-tri-0-acetyl-6-deoxy-5-thio-a-D-glucopyranoside [185802-82-8]... 

Ethyl 4, 0-benzylidene-l-thio-p-D-glucopyranoside, T-70 Ethyl 4-0-benzyl-2-0-methyl-l-thio-a-D-rhamnopyranoside, T-86 Ethyl 3-0-benzyl-l-thio-a-D-arabinofuranoside, T-57 Ethyl 4-0-benzyl-l-thio-a-D-rhamnopyranoside, T-86 Ethyl 5,6-bis-0-(4-chlorobenzyl)-3-0-propyl p-D-glucofuranoside, C-140 Ethyl bis(ethylthio)acetate, G-559 Ethyl cellulose, C-48 Ethyl 6-deoxymannoside, E-27 Ethyl 6-deoxy-3-0-methyl-p-L-glucopyranoside, D-142 Ethyl 4-deoxy-p-L-crji/ira-pentopyranoside, D-347 Ethyl 2,6-diacetamido-2,3,4,6-tetradeoxy-a-D-g/ cero-hex-4-enopyranoside, D-469... 

Isopropyl 3,4-O-isopropylidene-0E-L-f 7iAro-pentopyranosid-2-ulose, P-42 Isopropyl (methyl 2,3-0-isopropylidene-p-D-ribofuranosid)uronate, R-146 Isopropyl 2,3,4,5,6-penta-O-acetyl-D-galactonate, G-23 Isopropyl 1-thio-p-D-galactopyranoside, T-65 Isopropyl 1-thio-a-D-glucopyranoside, T-65... 

Methyl 4-acetamido-4-deoxy-a-L-sorbopyranoside, A-335 Methyl 2-acetamido-2-deoxy-a-D-talopyranoside, A-340 Methyl 3-acetamido-3-deoxy-a-D-talopyranoside, A-341 Methyl 2-acetamido-2-deoxy-5-thio-a-D-altropyranoside, A-345 Methyl 2-acetamido-2-deoxy-5-thio-p-D-altropyranoside, A-345 Methyl 2-acetamido-2-deoxy-5-thio-a-D-glucopyranoside, A-349 Methyl 2-acetamido-2-deoxy-6-0-tosyl-a-D-altropyranoside, A-164 Methyl 2-acetamido-2-deoxy-6-0-tosyl-a-D-glucopyranoside, M-144 Methyl 2-acetamido-2-deoxy-3-0-tosyl-a-D-idopyranoside, A-291 Methyl 2-acetamido-2-deoxy-3,4,6-tri-0-methyl-a-D-glucopyranoside, M-145 Methyl 4-acetamido-4-deoxy-a-D-g-/ycero -D-galacto-D-gluco -undecopyranoside, H-122... 

Methyl 3-acetamido-3-deoxy-p-D-glucopyranoside, A-267 Methyl 2-acetamido-2-deoxy-5-thio-a-D-glucopyranoside, A-349 Methyl 2-acetamido-3,6-di-0 -acetyl-2,4-dideoxy-4-fluoro-a-D-glucopyranoside, A-373... 

Methyl 3-0 -acetyl-2,4-dianiino-2,4,6-trideoxy-a-D-idopyranoside, D-480 Methyl 4-(acetylmethylamino)-4,6-dideoxy-a-D-glucopyranoside, A-382 Methyl 4-amino-4-deoxy-a-D-arabinopyranoside, A-179 Methyl 4-amino-4-deoxy-a-L-arabinopyranoside, A-179 Methyl 4-amino-4-deoxy-p-L-arabinopyranoside, A-179 Methyl 4-amino-4-deoxy-a-D-glucopyranosiduronic acid, SCI, A-276 Methyl 4-amino-4-deoxy-2,3-0 -isopropylidene-a-L-talopyranoside, A-342 Methyl 4-amino-4-deoxy-2-0-niesyl-a-L-lyxopyranoside, A-298 Methyl 4-amino-4-deoxy-a-L-sorbopyranoside, A-335 Methyl 4-amino-4-deoxy-5-thio-p-L-lyxopyranoside, A-350 Methyl 4-amino-4-deoxy-a-D-xylopyranoside, A-357 Methyl 4-amino-4,6-dideoxy-a-D-allopyranoside, A-365 Methyl 4-amino-4,6-dideoxy-p-D-allopyranoside, A-365 Methyl 4-amino-4,6-dideoxy-a-D-altropyranoside, A-370 Methyl 4-amino-4,6-dideoxy-a-D-galactopyranoside, A-377 Methyl 4-amino-4,6-dideoxy-a-D-glucopyranoside, A-382 Methyl 4-amino-4,6-dideoxy-a-D-idopyranoside, A-403 Methyl 4-amino-6-dideoxy-2,3-0-isopropylidene-a-L-talopyranoside, A 17... 

Methyl l,3,4-tri-0-acetyl-5-S -acetyl-5-thio-p-D-fructopyranoside, T-61 Methyl 2,3,4-tri-0-acetyl-6-deoxy-5-thio-a-D-glucopyranoside, D-373 Methyl 3,4,6-tri-0-acetyl-2-5-(2,3,4,6-tetra-0-acetyl-a-D-glucopyranosyl)-2-thio-p-D-glucopyranose, T-78 Methyl 2,3,4-tri-0-acetyl-5-thio-p-D-arabinopyranoside, T-58 Methyl 2,3,4-tri-0-acetyl-5-thio-p-D-lyxopyranoside, T-80 Methyl 2,3,4-tri-0-acetyl-5-thio-p-D-ribopyranoside, T-91... 

Methyl 2,3,6-tri-0-benzoyl-4-deoxy-4-thiocyano- -D-glucoside kept 6 hrs. at room temp, in a soln. of Na in dry methanol, and the crude intermediate treated with acetic anhydride in pyridine methyl 2,3,6-tri-0-acetyl-4-S-acetyl-4-thio-a-D-glucopyranoside. Y 81%. S. D. Gero and R. D. Guthrie, Soc. (C) 1967, 1761. 

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