Synthesis of N-acylated 7-amino-2,6,7-trideoxy-D-erythroheptopyranosides from methyl alpha-D-mannoside |
| |
Authors: | Wiedemeyer Kathrin Wünsch Bernhard |
| |
Institution: | Institut für Pharmazeutische und Medizinische Chemie der Westf?lischen Wilhelms-Universit?t Münster, Hittorfstrasse 58-62, D-48149 Münster, Germany. |
| |
Abstract: | Hexopyranoside methyl alpha-D-mannoside (8) was homologated to yield 7-(acylamino)-2,6,7-trideoxy-heptopyranosides 19-26. A crucial reaction step is the radical cleavage of benzylidene derivative 10 to obtain bromide 11. Since nucleophilic substitution of 11 with KCN provided the bicyclic nitrile 13 instead of nitrile 14, ketone 11 was protected as the dimethyl acetal 15. Nucleophilic substitution of 15 with KCN, subsequent hydrogenation with H2/Raney Ni and acylation with various carboxylic acid derivatives yielded 7-(acylamino)heptopyranosides 19-22. |
| |
Keywords: | Mannose 7-(Acylamino)heptopyranosides Radical cleavage of benzylidene acetal Nucleophilic substitution Dioxabicyclo[3 2 1]octane |
本文献已被 ScienceDirect PubMed 等数据库收录! |