SYNTHESES OF BIOLOGICALLY IMPORTANT CARBOHYDRATES .20. N-ACETYL-1,4-DI-O-ACETYL-BETA-DL-VANCOSAMINE

被引：18

作者：

DYONG, I

FRIEGE, H

机构：

[1] Organisch-Chemisches Institut der Universität Münster, Münster, D-4400

来源：

CHEMISCHE BERICHTE-RECUEIL | 1979年 / 112卷 / 09期

关键词：

D O I：

10.1002/cber.19791120922

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Die Claisen‐Umlagerung von (1‐methyl‐2‐butenyl)‐vinyl‐ether (3)liefert trans‐3‐Methyl‐4‐hexenal(4), dessen Ethylenacetal 5 mit Selen und Chloramin‐T zu den 3‐Methyl‐3‐tosylamino‐(6) und 3‐Methl‐6‐tosylamino‐Derivaten 7 aminiert wird. Nach Detosylierung von 6 und N‐Acetylierung wird trans‐3‐Acetylamino‐3‐methyl‐4‐hexenal‐ethylenacetal (9) zu 10/11 cis‐hydroxyliert. Abspaltung der Schutzgruppe an C‐1 und Peracetylierung liefert n‐Acetyl‐1,4‐di‐O‐acetyl‐β‐DL‐vancosamin (13), dessen Konstitution durch MS bewiesen und dessen lyxo‐Konfiguration durch 1 H‐NMR‐Untersuchungen weitgehend gesichert wird *). Copyright © 1979 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim

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页码：3273 / 3281

页数：9

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