Allopyranoside 2,3-0-isopropylidene

Preparation. D-Allose was obtained by alkaline followed by acid hydrolysis of the phenolic (3-D-allopyranoside esters (17 and 18) purified from leaves of Protea rubropilosa. The sugar was obtained crystalline and identified with an authentic sample prepared from D-ribose by the cyanohydrin reaction.763 A more-convenient preparation involves an oxidation-reduction sequence with l,2 5,6-di-0-isopropylidene-a-D-glucofuranose, followed by acid hydrolysis. 76b... 

Me glycoside, 3,4-O-isopropyUdene Methyl 2-chloro-2-deoxy-3,4-0-isopropylidene-ot-D-allopyranoside C10H17CIO5 252.694 Mp 60°. [ ]d +75.9 (CHCI3). 

Me glycoside, 4,6-O-isopropylidene Methyl 3-deoxy-3-fluoro-4,6-0-isopropylidene-P-D-allopyranoside [87585-99-7]... 

Benzyl 4-amino-4-deoxy-2,3-0-isopropylidene-a-D-mannofuranoside, A-314 Benzyl 2,3-anhydro-a-D-allopyranoside, A-484... 

Methyl 2,3-anhydro-4-bromo-4-deoxy-a-L-lyxopyranoside, B-84 Methyl 2,3-anhydro-4-bromo-4-deoxy-6- O -trityl-a-D-gulopyranoside, B-78 Methyl 2,3-anhydro-4-chloro-4-deoxy-a-L-xylopyranoside, C-110 Methyl 2,3-anhydro-6-deoxy-a-D-allopyranoside, A-516 Methyl 2,3-anhydro-6-deoxy-a-L-allopyranoside, A-516 Methyl 3,6-anhydro-2-deoxy-4,5 7,8-di-0-isopropylidene-D-g-/ycer(3-D-ia/o-octonate, M-174... 

Methyl 4,6- O -benzylidene-2,3- O -isopropylidene-a-D-allopyranoside, M-155 Methyl 4, 6 -0-benzylidene-p-maltoside, M-15 Methyl 4,6-D-benzylidenemannopyranoside, M-169 Methyl 4,6-0-benzylidene-2-0-mesyl-a-D-allopyranoside, M-155 Methyl l,3-0-benzylidene-4-0-mesyl-p-D-fructopyranoside, M-182 Methyl 4,6-0-benzylidene-2-0-mesyl-a-D-glucopyranoside, M-164 Methyl 4,6-0-benzylidene-2-0-mesyl-p-D-glucopyranoside, M-165 Methyl 4,6-0-benzylidene-3-0-mesyl-p-D-glucopyranoside, M-165 Methyl 4,6- 0 -benzylidene-2- O -mesyl-a-D-r o -hexopyranosid-3-ulose, M-167... 

Methyl 2-0-benzyl-3,4-0-isopropylidene-p-L-arabinopyranoside, M-197 Methyl 2-0-benzyl-3,4-O-isopropylidene-a-L-fucopyranoside, M-198 Methyl 3- 0 -benzyl-1,2- O -isopropylidene- p-L-idofuranuronate, 1-12 Methyl 5-0-benzyl-2,3-0-isopropylidene-a-D-lyxofuranoside, 1-70 Methyl 5-O-benzyl-2,3-O-isopropylidene-a-D-mannofuranoside, 1-71 Methyl 6-O-benzyl-2,3-O-isopropylidene-a-D-mannofuranoside, 1-71 Methyl 4-O-benzyl-2,3-O-isopropylidene-a-L-rhamnopyranoside, M-207 Methyl 2-O-benzyl-3,5-O-isopropylidene-a-D-xylofuranoside, M-216 Methyl 2-O-benzyl-3,5-O-isopropylidene-p-D-xylofuranoside, M-216 Methyl 3-0-benzyl-2-0-methyl-a-D-allopyranoside, M-148 Methyl 5-0-benzyl-2-0-methyl-a-D-glucofuranosidurono-6,3-lactone, G-539 Methyl 5-0-benzyl-2-0-methyl-p-D-glucofuranosidurono-6,3-lactone, G-539 Methyl 2,6-0-benzyl-3-0-methyl-a-D-mannopyranoside, M-271 Methyl 3-0-benzyl-2-O-methyl-6-0-tosyl-a-D-allopyranoside, M-148 Methyl 5-0-benzyl-3-0-methyl-a-D-xylofuranoside, M-216 Methyl 3-0-benzyl-a-L-rhamnopyranoside, M-207 Methyl 4-0-benzyl-a-L-rhamnopyranoside, M-207 Methyl 3-0-benzyl-p-L-ribofuranoside, M-208 Methyl 3-O-benzyl-4-O -(2,3,4-tri-O-benzyl-p-D-xylopyranosyl)-p-D-xylopyranoside, X-80... 

Methyl 6-deoxy-a-D-idopyranoside, D-238 Methyl 6-deoxy-p-L-idopyranoside, D-238 Methyl 6-deoxy-6-iodo-a-D-allopyranoside, D-245 Methyl 6-deoxy-6-iodo-p-D-allopyranoside, D-245 Methyl 2-deoxy-2-iodo-a-D-altropyranoside, D-246 Methyl 6-deoxy-6-iodo-2,3-di-0-mesyl-a-D-mannopyranoside, D-266 Methyl 4-deoxy-4-iodo-p-D-galactopyranoside, D-257 Methyl 6-deoxy-6-iodo-a-D-glucopyranoside, D-258 Methyl 6-deoxy-6-iodo-2,3-0 -isopropylidene-a-D-mannopyranoside, D-266 Methyl 6-deoxy-6-iodo-2,3-<7-isopropylidene-4-O-mesyl-0(-D-mannopyranoside, D-266... 

Methyl 2-deoxy-4,5-0-isopropylidene-7-0-trityl-D-a//o-heptonate, A-532 Methyl 6-deoxymannofuranoside, M-206 Methyl 6-deoxymannopyranoside, M-207 Methyl 6-deoxy-4-0-mesyl-a-D-talopyranoside, D-372 Methyl 3-deoxy-3-(A-methylacetamido)-a-D-arabinofuranoside, D-293 Methyl 3-deoxy-3-(A-methylacetamido)-p-D-xylopyranoside, D-294 Methyl 6-deoxy-2-0-methyl-a-D-allopyranoside, D-34 Methyl 6-deoxy-3-0-methyl-a-D-allopyranoside, D-34 Methyl 6-deoxy-2-0-methyl-p-D-allopyranoside, D-34 Methyl 6-deoxy-3-0-methyl-p-D-allopyranosyl-(l 4)-2-deoxy-a-D-arabino -hexopyranoside, D-774 Methyl 6-deoxy-4-0-methyl-a-D-altropyranoside, D-37 Methyl 6-deoxy-4-0-methyl-p-D-altropyranoside, D-37 Methyl 3-deoxy-3-(methylamino)-a-D-arabinofuranoside, D-293 Methyl 3-deoxy-3-(methylamino)-a-D-arabinopyranoside, D-293 Methyl 3-deoxy-3-(methylamino)-a-L-arabinopyranoside, D-293 Methyl 3-deoxy-3-(methylamino)-p-L-arabinopyranoside, D-293 Methyl 3-deoxy-3-(methylamino)-a-D-xylopyranoside, D-294 Methyl 3-deoxy-3-(methylamino)-p-D-xylopyranoside, D-294 Methyl 3-deoxy-3-(methylamino)-p-L-xylopyranoside, D-294 Methyl 6-deoxy-4-0-methyl-a-D-glucopyranoside, D-142 Methyl 6-deoxy-3-0-methyl-a-D-glucopyranoside, D-142 Methyl 6-deoxy-3-0-methyl-p-D-glucopyranoside, D-142 Methyl 3-deoxy-3-C-methyl-a-D-glucopyranoside, D-301... 

Diisopropylidene-5-thio-a-D-allofuranose, T-54 l,2 5,6-Di-0-isopropylidene-3-0-tosyl-a-D-allofuranose, 1-58 Ethyl 2,3-dideoxy-2,3-C-methylene-a-D-allopyranoside, D-626 Helicide, H-3... 

Methyl 3-acetamido-3-deoxy-a-D-allofnranoside, A-157 Methyl 3-acetamido-3-deoxy-p-D-allofnranoside, A-157 Methyl 4-acetamido-4,6-dideoxy-a-D-allopyranoside, A-365 Methyl 4-acetamido-4,6-dideoxy-p-D-allopyranoside, A-365 Methyl 3-acetamido-2,5,6-tri-0-acetyl-3-deoxy-p-D-allofuranoside, A-157 Methyl 3-acetamido-2,4,6-tri-0-acetyl-3-deoxy-a-D-allopyranoside, A-157 Methyl 3-acetamido-2,4,6-tri-0-acetyl-3-deoxy-p-D-allopyranoside, A-157 Methyl 2-0-acetyl-4,6-0-benzylidene-a-D-allopyranoside, M-155 Methyl 2-0-acetyl-4,6-0-(J )-benzylidene-3-chloro-3-deoxy-p-D-allopyranoside, C-71 Methyl a-D-allofuranoside, M-148 Methyl p-D-allofuranoside, M-148 Methyl a-D-allopyranoside, M-148 Methyl p-D-allopyranoside, M-148 Methyl 3-amino-3-deoxy-p-D-allofnranoside, A-157 Methyl 3-amino-3-deoxy-a-D-allopyranoside, A-157 Methyl 3-amino-3-deoxy-p-D-allopyranoside, A-157 Methyl 4-amino-4,6-dideoxy-a-D-allopyranoside, A-365 Methyl 4-amino-4,6-dideoxy-p-D-allopyranoside, A-365 Methyl 5,6-anhydro-2,3-0-isopropylidene-p-L-allofuranoside, M-148 Methyl 2-0-benzoyl-4,6-0-benzylidene-a-D-allopyranoside, M-155 Methyl 6-O-benzoyl-3,4-O -isopropylidene-2-O-tosyl-a-D-allopyranoside, M-148... 

Methyl 4,6-0-benzylidene-3-deoxy-3-iodo-p-D-allopyranoside, D-243 Methyl 4,6-0-benzylidene-2,3-0-isopropylidene-a-D-allopyranoside,... 

Methyl 3,4-0-isopropylidene-2-0-tosyl-a-D-allopyranoside, M-148 Methyl 2,3,4,6-tetra-O-acetyl-a-D-allopyranoside, M-148 Methyl 2,3,4,5-tetra-O-acetyl-p-D-alloseptanoside, A-87 Methyl 2,3,4,6-tetra-0-acetyl-5-thio-a-D-allopyranoside, T-54 Methyl 2,3,4,6-tetra-0-acetyl-5-thio-p-D-allopyranoside, T-54 Methyl 5-thio-a-D-allopyranoside, T-54 Methyl 5-thio-p-D-allopyranoside, T-54 Methyl 2-0-tosyl-a-D-allopyranoside, M-148... 

Methyl 4-acetamido-4,6-dideoxy-a-D-allopyranoside, A-365 Methyl 4-acetamido-4,6-dideoxy-p-D-allopyranoside, A-365 Methyl 4-acetamido-4,6-dideoxy-a-D-altropyranoside, A-370 Methyl 4-acetamido-4,6-dideoxy-a-D-idopyranoside, A-403 Methyl 4-acetamido-4,6-dideoxy-2,3-0-isopropylidene-a-D-talopyranoside, A-417... 

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 2-C-hydroxymethyl-p-i>ribopyranoside, H-ISI Methyl 2,3-0-isopropylid e-3 -methyl-i>apio-p-D-furanoside, A-785 Methyl 2,3-0-isopropylidene-l -tosyl-D-apio-p-D-furanoside, A-7S5 Methyl 2-C-methyl-i>arabiiiopyranoside, M-229 Methyl 2-C-methyl-p-L-arabiiiopyranoside, M-229 Methyl 4-C-methyl-a-i>glucopyranosidiironic acid, M-260 Methyl 3-C-methyl-2-0-methyI-a-D-allopyraiioside, M-224 Methyl 3-C-methyl-2-0-methyl-4,6-di-0-tosyl-a-i>allopyranoside, M-224 Methyl 3-C-methyl-2-0-methyl-6-0-tosyl-a-i>allopyraiioside, M-224 Methyl 2-C-methyl-p-D-ribofuranoside, M-286 Methyl 2-C-methyl-p-L-ribopyranoside, M-286 Methyl 2,3,4,6-tetradeoxy-4-(methoxycarbonylamino)-3-C-methyl-3-nitro-a-i>xyfo-hexopyranoside, K-16 Methyl 2,3,4, tetradeoxy-4-(methoxycarbonylamino)-3-C-methyl-3-nitro-p-i>xyfo-hexopyranoside, K-16 Methyl 2,3,4-tri-0-acetyl-6-deoxy-3-C-methyl-a-i>niannopyranoside, D-308... 

Two polymorphs of a,a-trehalose octacetate monohydrate, 4,4 -dideoxy-a,a- ty/o-trehalose, methyl 2,3,4,6,2, 4, 6 -hepta-C -acetyl-a-laminaribinoside, 2 3,3 -dideoxy-a,a-flrflbjno-trehalosc. 3 Methyl 2,3-0-isopropylidene-5-0-tosyl-P-D-ribofuranoside 2, the 7-carbon glycoside 3 (see Chapter 17), C-glycosidic furanoside 4 (see Chapter 14) the oxazoline derivative 5 and methyl 1,6-di-0-(4-bromobenzoyl)-3,4-di-0-(4-methoxycinnamoyl)-P-D-fructofuranoside. Di-(3-deoxy-D-g/yccro-pcntulose)-l,2 2,r-dianhydridc, methyl 4,6-benzylidene-a-D-allopyranoside, methyl-2,3,4-tri-0-acctyl-a-L-rhamnopyranoside, l 2-(indol-3-yl)ethyl 2,3,4-tri-O-acetyl-a-L-... 

Deoxygenation, of sugars can also be achieved by way of thio-sugar precursors, which can be desulphurized with Raney nickel or sodium in liquid ammonia or tributyltin hydride. This approach has been used to synthesize methyl 2-amino-2,3-dideoxy-4,6-0-isopropylidene-a-D-ribo-hexopyranoside (278) from the 3-S-phenylthio-a-D-allopyranoside obtained when the 3-triflate (279) reacted with sodium benzenethiolate at 5°C—in this instance, desulphuration was best achieved with sodium in liquid ammonia. ... 

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