Highly Stereoselective Synthesis of Primary, Secondary, and Tertiary 伪-S-Sialosides under Lewis Acidic Conditions

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• 作者：Amandine Noel ; Bernard Delpech ; David Crich
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：August 17, 2012
• 年：2012
• 卷：14
• 期：16
• 页码：4138-4141
• 全文大小：255K
• 年卷期：v.14,no.16(August 17, 2012)
• ISSN：1523-7052

文摘

N-Acetyl 4-O,5-N-oxazolidinone protected sialyl phosphates of either anomeric configuration are excellent donors for the formation of 伪-S-sialosides at 鈭?8 掳C in dichloromethane with primary, secondary, and tertiary thiols including galactose 3-, 4-, and 6-thiols. The reactions, which proceed under typical Lewis acid promoted glycosylation conditions, are highly 伪-selective and do not suffer from competing elimination of the phosphate.