ENANTIOMERICALLY PURE, HIGHLY FUNCTIONALIZED TETRAHYDROFURANS FROM SIMPLE CARBOHYDRATE PRECURSORS

被引：17

作者：

LUNDT, I

FRANK, H

机构：

[1] Department of Organic Chemistry, The Technical University of Denmark

来源：

TETRAHEDRON | 1994年 / 50卷 / 46期

关键词：

D O I：

10.1016/S0040-4020(01)89337-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto-, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water. The 6-bromo-6-deoxy-D-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature. Likewise, the 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydrides, when heated in water. The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.

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页码：13285 / 13298

页数：14

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