The reaction of pyranoside 2-uloses with DAST revised.: Synthesis of 1-fluoro-ketofuranosyl fluorides and their reactivity with alcohols

被引：17

作者：

Aghmiz, ML

Díaz, Y

Jana, GH

Matheu, MI

Echarri, R

Castillón, S

Jimeno, ML

机构：

[1] Univ Rovira & Virgili, Dept Quim, E-43005 Tarragona, Spain

[2] CSIC, Ctr Quim Organ Manuel Lora Tamayo, E-28006 Madrid, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 31期

关键词：

carbohydrates; uloses; fluorination; diethylaminosulfur trifluoride; glycosylation; spiroacetals;

D O I：

10.1016/S0040-4020(01)00620-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have reinvestigated the reaction of alpha -pyranosides-2-uloses 13, 14, 19 and 24 with DAST and shown that the 1,2-difluorinated compounds 17, 18 and 25 are produced by a ring-contraction reaction. The reaction of 18 with benzyl alcohol gives the tri-benzyl derivative 26 or compound 27, depending on the reaction conditions. Treating 17 with 2-naphthol produced the spiranic compounds 29-31. The reaction of 17 with bis(trimethylsilyl)uracil produced the mononucleoside 28, which preserves the fluorine atom in the more substituted carbon. (C) 2001 Elsevier Science Ltd. All rights reserved.

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收藏

页码：6733 / 6743

页数：11

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