Synthesis of the first 1-azaanalogues of L-sugars.

✍ Scribed by Anja Hansen; Tina M. Tagmose

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 733 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(96)01012-5

✦ Synopsis

1. or I-aza-2deoxy-L-carbafucose was synthesized from L-arabinose in 9 steps. L-Arabinose was converted to the benzyl glycoside, and then to the 3,4-acetonide. Oxidation of the 2-hydroxygroup followed by Wittig methylenation gave benzyl2-deoxy-3,4-O-isopropylidene-2-methylene-P-~-erythro-pentopyranoside (6). Stereoselective hydrogenation followed by reductive debenzylation and reduction led to 2-deoxy-3,4-0-isopropyopylidene-2-C-methyl-L-ribitol(9), which was ditosylated and treated with bet&amine to give a piperidine. Finally deprotection gave 1. 1,3,5-Trideoxy-2-Chydroxymethyl-l,5-imino-D-eryfhro-pentitol(2) was prepared from lactose in 7 steps. 2,2'-U-isopropylidene-5-O-(4methylbenzenesulphonyl)-o-isosaccharino-I,4-lactone ( 14) was reacted with ammonia to give the 1,5-lactam. Deprotection and reduction gave 2. Azasugar 1 was found to be a potent inhibitor of a-fucosidase.