THE SYNTHESIS OF 2,3-DIDEOXY-2-FLUORO-3-C-METHYLPENTOSE-CONTAINING NUCLEOSIDES VIA [3,3]-SIGMATROPIC REARRANGEMENTS

被引：8

作者：

ARAKI, K ^{[1
]}

YUN, WQ ^{[1
]}

OTOOLE, J ^{[1
]}

TOSCANO, PJ ^{[1
]}

WELCH, JT ^{[1
]}

机构：

[1] SUNY ALBANY, DEPT CHEM, 1400 WASHINGTON AVE, ALBANY, NY 12222 USA

来源：

CARBOHYDRATE RESEARCH | 1993年 / 249卷 / 01期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0008-6215(93)84067-G

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：

[3,3]-Sigmatropic rearrangement of in situ-formed [0,0]-silyl ketene acetals of butenyl fluoroacetates was used as the key step in the synthesis of racemic 2,3-dideoxy-2-fluoro-3-C-methylpentofuranoses. The product pentofuranoses were transformed further into pyrimidine and purine nucleosides. The conformations of the synthetic carbohydrates were confirmed by single-crystal X-ray diffraction studies and indicated that previous structural assignments made by NMR were in error.

引用

页码：139 / 161

页数：23

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