Xylofuranose, 5-acetamido-5-deoxy

It is not requisite that the anion eliminated in the step 19 to 20 be a hydroxyl ion, because acid hydrolysis of 5-amino-5-deoxy-l,2-0-isopropylidene - 3 - O - (methylsulfonyl )-a- D -xylofuranose likewise yields 3-pyridinol (21). On subjection to acid hydrolytic conditions which remove the 2V-acetyl group, such N-acetyl derivatives as 5-acetamido-5-deoxy-a-D-xylopyranose (see p. 167) are immediately transformed, through 17, into 3-pyridinol (21). Furthermore, acid hydrolysis of methyl 5-acetamido-5-deoxy-2,3,4-tri-0-methyl-a-D-... 

The tautomeric relationships have been investigated for all four of the 5-acetamido-5-deoxypentoses. 5-Acetamido-5-deoxy-l,2-0-iso-propylidene-a-D-xylofuranose (161) is obtainable by reaction of 1,2-O-isopropylidene-5-O-p-tolylsulfonyl-a-D-xylofuranose with ammonia or sodium azide, followed by acetylation of the amino compound. The preparation of larger amounts is more suitably... 

A nucleoside derivative of 4-acetamido-4-deoxy-D-xyIofuranose was synthesized by a series of reactions. Partial benzoylation of methyl )8-L-arabinopyranoside produces " methyl 2,3-di-0-benzoyl-j3-L-arabinopyranoside. p-Toluenesulfonylation at 0-4, followed by displacement with sodium azide, gives methyl 4-azido-2,3-di-0-benzoyl-4-deoxy-a-D-xylopyranoside. Hydrogenation, debenzoylation, N-acetylation, and acetolysis yield 4-acetamido-l,2,3,5-tetra-0-acetyl-4-deoxy-D-xylofuranose (D-enantiomorph of 191), which reacts in the presence of titanium tetrachloride in chloroform with chloromercuri-(6-benzoyladenine), giving, after deacylation, 9-(4-acetamido-4-deoxy-)8-D-xylofuranosyl)adenine. ... 

O-Isopropylidene, 5-benzoyl, N-Ac. 4-Acetamido-5-0-benzoyl-4-deoxy-l, 2-O-isopropylidene-a-D-xylofuranose [91876-95-8]... 

Acetamido-l,2-0-cyclobexylidene-5-deoxy-a-D-xylofuranose, A-358 2-Acetamido-2-deoxy-6- O -(2-acetamido-2-deoxy- P-D-galactopyranosyl)-D-galactose, A-170... 

Acetamido-l,2,4-tri-0-acetyI-3-deoxy-5-thio-a-i>xylopyranose, A-352 5-Acetamido-l,2,3-tri-0-acetyI-5-deoxy-D-xylofuranose, A-358... 

Acetamido 4-deoxy-l,2-0-isopropylidene-a-D-xylofuranose, A-357 4-Acetamido-4-deoxy-5-thio-L-Iyxopyranose, A-3 4-Acetamido-2,3-di-0-acetyI-l,6-anhydro-4-deoxy-p-D-mannopyranose, A-314... 

Acetamido-5-deoxy-1,2-0 -isopropylidene-a-D-xylofnranose, A-358 5-Acetamido-5-deoxy-a-D-lyxopyranose, A-299 5-Acetamido-5-deoxy-p-D-ribopyranose, A-332 5-Acetamido-5-deoxy-D-xylofuranose, A-358 5-Acetamido-5-deoxy-D-xylopyranose, A-358 5-Acetamido-2,3-di-0-acetyl-l,6-anhydro-5-deoxy-p-L-altrofuranose,... 

Reduction of the 3-C-cyano 3-sulphonate derivative (118) with lithium aluminium hydride furnished the branched-chain sugar (119) and the spiro-epimine (120), which, on further reduction and 7V-acetylation, gave 3-acetamido-3-deoxy-l,2 5,6-di-(7-isopropylidene-3-C-methyl-a-D-glucofuranose. The latter branched-chain amino-sugar was also converted into related o-xylofuranose derivatives by a conventional chain-shortening procedure, following removal of the 5,6-0-isopropylidene group. 

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