Lanthanide triflates/N-iodosuccinimide for chemoselective coupling of n-pentenyl donors in oligosaccharide assembly

被引：26

作者：

Jayaprakash, KN ^{[1
]}

Fraser-Reid, B ^{[1
]}

机构：

[1] Nat Prod & Glyotechnol Res Inst Inc, NPG, Durham, NC 27706 USA

来源：

SYNLETT | 2004年 / 02期

关键词：

lanthanide triflates; N-iodosuccinimide; n-pentenyl glycosides;

D O I：

10.1055/s-2003-44999

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Armed n-pentenyl glycosides (NPGs) react (a) readily with scandium and indium (111) triflates, (b) moderately with samarium and lanthanum counterparts, and (c) not at all with ytterbium counterpart. However the last salt reacts readily with n-pentenyl orthoesters (NPOE). These chemoselectivities of n-pentenyl donors towards lanthanide salts therefore permit hydroxyl-bearing armed NPGs to function as acceptors towards NPOE donors. This concept is demonstrated by synthesis of a tetrasaccharide.

引用

页码：301 / 305

页数：5

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