Efficient synthesis of alpha,omega-dibromodideoxyalditols as precursors for alpha,omega-dithioalkylalditols

被引：31

作者：

CrombezRobert, C ^{[1
]}

Benazza, M ^{[1
]}

Frechou, C ^{[1
]}

Demailly, G ^{[1
]}

机构：

[1] UNIV PICARDIE,CHIM ORGAN LAB,F-80039 AMIENS,FRANCE

来源：

CARBOHYDRATE RESEARCH | 1997年 / 303卷 / 03期

关键词：

alditols; alpha; omega-dibromoalditols; omega-dithioalkylalditols; thioetherification; regioselective bromination; acetoxonium ion;

D O I：

10.1016/S0008-6215(97)00151-1

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：

The regioselective bromination of unprotected alditols (D-arabinitol, xylitol, ribitol, D-glucitol, and D-mannitol) was achieved with acetyl bromide as the brominating reagent. The alpha,omega-dibromodideoxyalditols were isolated after acetylation in good overall yields (51-80%). 1,5-Dithioalkylpentitols, 1,6-dithioalkyl-D-mannitol, and D-glucitol were obtained from the dibromo derivatives and sodium alkanethiolates (with R = n-butyl, n-octyl, n-dodecyl, and n-hexadecyl). (C) 1997 Published by Elsevier Science Ltd.

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页码：359 / 365

页数：7

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