Gram-Scale Synthesis of an Armed Colitose Thioglycoside

作者:Lloyd Dina; Bennett Clay S*
来源:Journal of Organic Chemistry, 2014, 79(20): 9826-9829.
DOI:10.1021/jo501472v

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.

  • 出版日期2014-10-17