SYNTHESIS OF 3'-DEOXY-3'-FLUOROKANAMYCIN-A AND 3',4'-DIDEOXY-3'-FLUOROKANAMYCIN-A

被引：16

作者：

TAKAHASHI, Y ^{[1
]}

TSUCHIYA, T ^{[1
]}

UMEZAWA, S ^{[1
]}

UMEZAWA, H ^{[1
]}

机构：

[1] INST BIOORGAN CHEM,1614 IDA,NAKAHARA KU,KAWASAKI 211,JAPAN

来源：

CARBOHYDRATE RESEARCH | 1991年 / 210卷

关键词：

D O I：

10.1016/0008-6215(91)80124-6

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：

3'-Deoxy-3'-fluorokanamycin A (14) has been prepared by condensation of 6-azido-2,4-di-O-benzyl-3,6-dideoxy-3-fluoro-alpha-D-glucopyranosyl bromide (8) and 6-O-(2-O-acetyl-4,6-O-cyclohexylidene-3-deoxy-3-de-oxy-3-tosylamino-alpha-D-glucopyranosyl)-2-deoxy-1,3-di-N-tosylstreptamine (10). Compound 8 was obtained from 3-deoxy-3-fluoro-1,2:5,6-di-O-isopropylidene-D-glucofuranose in seven steps. 3',4'-Dideoxy-3'-fluoro-kanamycin A (22) has been prepared from 12 through selective 4'-chlorodeoxygenation, a key reaction. Both 14 and 22 were more active than 3'-deoxykanamycin A against both sensitive and resistant bacteria.

引用

页码：221 / 232

页数：12

共 10 条

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