SYNTHESIS OF THE DECULOPYRANOSONIC ACID ANALOG OF N-ACETYLNEURAMINIC ACID, ITS 5-EPIMER AND 6-EPIMER, AND OF 5-ACETAMIDO-1,3,5-TRIDEOXY-D-GLYCERO-D-GALACTO-NON-2-ULOPYRANOSE

被引：8

作者：

HAGEDORN, HW ^{[1
]}

MERTEN, H ^{[1
]}

BROSSMER, R ^{[1
]}

机构：

[1] UNIV HEIDELBERG,INST BIOCHEM 2,NEUENHEIMER FELD 328,W-6900 HEIDELBERG,GERMANY

来源：

CARBOHYDRATE RESEARCH | 1992年 / 236卷

关键词：

D O I：

10.1016/0008-6215(92)85008-N

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Condensation of 2-acetamido-2-deoxy-5,6-O-isopropylidene-D-mannofuranose with disodium acetonedicarboxylate and subsequent esterification with diphenyldiazomethane yielded diphenylmethyl 6-acetamido-2,4,6-trideoxy-D-glycero-beta-D-galacto-dec-3-ulopyranosonate (3), and its 5- and 6-epimer. Hydrogenation gave the corresponding free acids. Hydrogenation of ester 3 and working-up under alkaline conditions afforded stable ammonium 6-acetamido-2,4.6-trideoxy-D-glycero-beta-D-galacto-dec-3-ulopyranosonate which, on heating, led to an anomeric mixture of 5-acetamido-1,3,5-trideoxy-D-glycero-D-galacto-non-2-ulopyranose.

引用

页码：89 / 96

页数：8

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