Synthesis of dibekacin analogs containing 3-oxa- and 3-aza-2,3,4-trideoxy-D-glycero-hexopyranose

被引：3

作者：

Kuwahara, R ^{[1
]}

Tsuchiya, T ^{[1
]}

机构：

[1] INST BIOORGAN CHEM,NAKAHARA KU,KAWASAKI,KANAGAWA,JAPAN

来源：

CARBOHYDRATE RESEARCH | 1996年 / 293卷 / 01期

关键词：

aminoglycoside antibiotic; 5-deoxy-5-fluorination; glycosylation; Pb(OAc)(4) oxidation; reductive amination; Na in liquid NH3; STRUCTURE-TOXICITY RELATIONSHIPS; DERIVATIVES;

D O I：

10.1016/0008-6215(96)00176-0

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：

6-O-(3-Oxa-2,3,4-trideoxy-alpha-D-glycero-hexopyranosyl) derivatives (10 and 17) of both 3',4'-dideoxyneamine and 5-epifluoro-5,3',4'-trideoxyneamine have been prepared by coupling ethyl 6-O-benzyl-3-oxa-2,3,4-trideoxy-1-thio-D-glycero-hexopyranoside (5) with suitable aglycons. The corresponding 3 ''-aza derivative (19) of dibekacin (6) was prepared by oxidation of 1,3,2',6'-tetra-N-tosyldibekacin (7) with Pb(OAc)(4) followed by treatment with NH4OAc and reduction with NaBH3CN. Related ring-opening compounds (11 and 25) were also prepared. (C) 1996 Elsevier Science Ltd.

引用

页码：15 / 30

页数：16

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