Addition Reactions of Benzenesulfinic Acid with Glycals and 1,2-Dibromosugars

被引：10

作者：

Basava, Vikram ^{[1
]}

Flores, Broc ^{[1
]}

Giovine, Matthew ^{[1
]}

Licisyn, Thomas ^{[1
]}

Walck, Katelyn ^{[1
]}

Boyko, Walter ^{[1
]}

Giuliano, Robert ^{[1
]}

机构：

[1] Villanova Univ, Dept Chem, Villanova, PA 19085 USA

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2008年 / 27卷 / 07期

关键词：

Benzenesulfinic acid; glycosyl phenylsulfones; carbohydrate sulfinate esters;

D O I：

10.1080/07328300802374805

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 addition of benzenesulfinic acid to glycals was investigated under various conditions, and optimized yields of the glycosyl phenylsulfone products were obtained in the presence of tin tetrachloride as a catalyst. Double bond shift (Ferrier rearrangement) occurred in all cases except amicetal, which lacks a substituent at the allylic carbon. Glycosylation of benzenesulfinic acid with 1,2-dibromides was carried out using silver triflate as the promoter, and gave sulfinate esters as products by reaction at oxygen rather than at sulfur. The sulfinate esters were obtained as mixtures of stereoisomers at the stereogenic sulfur atom. Trapping of the sulfinates with carboxylate nucleophiles was observed during attempted oxidation with MCPBA.

引用

页码：389 / 400

页数：12

共 25 条

[1] Fragmentation of carbohydrate anomeric alkoxyl radicals.: Synthesis of highly functionalized chiral vinyl sulfones [J].