Scavenging byproducts in the sulfoxide glycosylation reaction: Application to the synthesis of ciclamycin 0

被引：74

作者：

Gildersleeve, J ^{[1
]}

Smith, A ^{[1
]}

Sakurai, K ^{[1
]}

Raghavan, S ^{[1
]}

Kahne, D ^{[1
]}

机构：

[1] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1999年 / 121卷 / 26期

关键词：

D O I：

10.1021/ja990690a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed a direct and efficient route for the synthesis of ciclamycin 0 using the sulfoxide glycosylation reaction to form the glycosidic linkages. In the course of completing the synthesis of ciclamycin 0, we developed new glycosylation conditions that improve the outcome of the sulfoxide reaction. The conditions involve the addition of agents that scavenge phenylsulfenyl triflate, a highly reactive byproduct that forms following activation of anomeric sulfoxides with triflic anhydride.

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页码：6176 / 6182

页数：7

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