Synthesis of specifically deoxygenated analogues of the methyl α-glycoside of the intracatenary monosaccharide repeating unit of the O-polysaccharide of Vibrio cholerae O:1
✍ Scribed by Makoto Gotoh; Pavol Kováč
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- English
- Weight
- 713 KB
- Volume
- 268
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
Treatment of methyl Ot-D-perosaminide (1) with y-butyrolactone gave the 2'-deoxy analogue of methyl 4,6-dideoxy-4-(3-deoxy-L-glycero-tetronamido)-a-D-mannopyranoside (13), the methyl a-glycoside of the intracatenary monosaccharide repeating unit of the O-polysaccharide of Vibrio cholerae O:1. The analogous 4'-deoxy derivative was obtained by hydrogenolysis of a 4'-chlorodeoxy precursor, obtained by chlorination of methyl 2,3-di-O-benzyl-4-(2-O-benzyl-3-deoxy-Lglycero-tetronamido)-4,6-dideoxy-a-D-mannopyranoside with methanesulfonyl chloride in DMF. To obtain the 3-deoxy analogue of 13, methyl 4-amino-2-O-benzyl-4,6-dideoxy-3-O-p-methoxybenzyl-ot-D-mannopyranoside was converted into methyl 2-O-benzyl-4,6-dideoxy-4-(2,4-di-O-benzyl-3-deoxy-L-glycero-tetronamido)-ct-D-mannopyranoside, which was deoxygenated via the corresponding 3-O-(imidazol-l-ylthiocarbonyl) derivative. Subsequent catalytic debenzylation gave the deoxy compound (24). In an alternative synthesis, which is also generally useful for the preparation of 4-N-acyl-3-deoxy derivatives of 1, methyl 4-azido-4,6-dideoxy-t~-D-mannopyranoside was converted through a series of transformations into methyl 4-amino-2-O-benzyl-3,4,6-tri-Synthesis of ligands related to the Vibrio cholerae O-specific antigen. Part 4. For Part 3 see Ref. [1].
📜 SIMILAR VOLUMES
Methyl 4-azido-4,6-dideoxy-3-O-benzyl-ct-D-mannopyranoside and its analogous 3-O-(4methoxybenzyl) derivative were methylated and the 2-O-methyl derivatives formed were convetted into methyl 4-amino-4,6-dideoxy-2-O-methyl-a-o-mannopyranoside. Reaction of the latter with 3-deoxy-L-glycero-tetronolacto
## Abstract The title disaccharide, 2‐{2‐{2‐[(2‐ethoxy‐3,4‐dioxocyclobut‐1‐en‐1‐yl)amino]ethoxy}ethoxy}ethyl 2‐__O__‐(3,6‐dideoxy‐__α__‐L‐__xylo__‐hexopyranosyl)‐__β__‐d‐galactopyranoside cyclic 4,6‐(potassium phosphate) (**2**), was synthesized from the two isomeric linker‐equipped galactose accep
Methyl 4-(3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-2-O-methyl-alpha-D- mannopyranoside was acetylated, and the fully protected methyl glycoside was treated with dichloromethyl methyl ether-ZnCl2 (DCMME-ZnCl2) reagent to give 3-O-acetyl-4-(2,4-di-O-acetyl-3- deoxy-L-glycero-tetronamido)-4,6-dideoxy