Intervention of catalytic amounts of water in the allylic rearrrangements of glycal derivatives

被引：14

作者：

Blattner, R ^{[1
]}

Ferrier, RJ ^{[1
]}

Furneaux, RH ^{[1
]}

机构：

[1] Ind Res Ltd, Lower Hutt, New Zealand

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 02期

关键词：

D O I：

10.1016/S0957-4166(99)00499-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

It is confirmed that tri-O-acetyl-D-gluca1 with thiophenol in the presence of BF3. OEt2 as catalyst gives the allylically rearranged S-phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-alpha- and beta-D-erthyrro-hex-2-enopyranosides as the main products, and now demonstrated that the presence of catalytic proportions of water diverts the reaction in favour of the isomeric S-phenyl 4,6-di-O-acetyl-2-deoxy-3-phenylthio-1-thio-D-arabino- and -D-ribo-hexopyranosides, It is proposed that these products are formed from an intermediate enal. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：379 / 383

页数：5

共 19 条

[1]

[Anonymous], 1995, MONOSACCHARIDES THEI

[2] REACTION OF UNSATURATED CARBOHYDRATE DERIVATIVES WITH METHANOL AND BORON TRIFLUORIDE [J].