A SYNTHETIC STUDY OF METHYL 3-DEOXY-3-FLUORO-ALPHA-D-GLUCO-PYRANOSIDES FROM METHYL 2,3-ANHYDRO-ALPHA-D-ALLOPYRANOSIDES, AND SYNTHESIS OF 3'-DEOXY-3'-FLUOROKANAMYCIN-A AND 3'-CHLORO-3'-DEOXYKANAMYCIN-A

被引：17

作者：

UMEMURA, E ^{[1
]}

TSUCHIYA, T ^{[1
]}

KOBAYASHI, Y ^{[1
]}

TANAKA, K ^{[1
]}

机构：

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

来源：

CARBOHYDRATE RESEARCH | 1992年 / 224卷

关键词：

D O I：

10.1016/0008-6215(92)84101-W

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：

Reactions of 4,6-disubstituted 2,3-anhydro-alpha-D-allopyranosides with potassium hydrogenfluoride (KHF2) in ethane-1,2-diol gave, by oxirane-ring opening, the corresponding 2-deoxy-2-fluoro-alpha-D-altro- and 3-deoxy-3-fluoro-alpha-D-gluco-pyranosyl derivatives, with the latter always in preponderance. The influence of the substituents at C-4 and C-6 on the D-gluco-D-altro ratio (r) have been studied by molecular mechanics, and the discrepancy between the experimental and calculated r values has been positively utilized to measure the effects of solvation and hydrogen bonding relative to the C-4 and C-6 substituents. By application of this reaction, 3'-deoxy-3'-fluorokanamycin A has been prepared by treatment of a 2',3'-anhydro-3'-epikanamycin A derivative (35) with KHF2. 3'-Chloro-3'-deoxykanamycin A was also prepared.

引用

页码：141 / 163

页数：23

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