Gram-Scale Synthesis of an Armed Colitose Thioglycoside

被引：8
|
作者：
Lloyd, Dina [1 ]
Bennett, Clay S. [1 ]
机构：
[1] Tufts Univ, Dept Chem, Medford, MA 02155 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 20期
基金：
美国国家科学基金会;
关键词：
LIPOPOLYSACCHARIDES; 3-DEOXY-L-FUCOSE;
D O I：
10.1021/jo501472v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A concise gram-scale synthesis of protected colitose thioglycosides for use in bacterial carbohydrate antigen synthesis is described. The synthesis proceeds in six steps and 59-70% overall yield from commercially available l-fucose, making it the most efficient route reported to date. Key steps include regioselective installation of a thiocarbonate using catalytic dioctyltin dichloride (10 mol%) and a tris(trimethylsilyl)silane-mediated radical deoxygenation.
引用
收藏
页码：9826 / 9829
页数：4
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