通过 4,5-O-碳酸酯保护基对 alpha-酮去氧-D-甘油-D-半乳糖-壬酮糖苷进行立体选择性合成。
Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group.
机构信息
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA.
出版信息
Angew Chem Int Ed Engl. 2010 Apr 12;49(17):3049-52. doi: 10.1002/anie.200907178.
Abstract
[Image: see text] A 1-adamantyl thioglycoside derivative of KDN, derived from -acetylneuraminic acid, carrying a 3,4--carbonate protecting group is a highy efficient and α-selective KDN donor on activation with NIS and TfOH in dichloromethane and acetonitrile at −78 °C. Glycosylations conducted with this protecting group do not suffer from competing glycal formation. Seven examples are given, including the use of galactose 3- and 6-hydroxy groups.
摘要
[图像：见正文] 1-金刚烷基硫代糖苷衍生物 KDN 来源于 N-乙酰神经氨酸，带有 3,4--碳酸酯保护基团，在 NIS 和 TfOH 的作用下，在−78°C 的二氯甲烷和乙腈中是高效且 α-选择性的 KDN 供体。使用该保护基进行的糖苷化反应不会受到竞争糖醛形成的影响。给出了七个实例，包括使用半乳糖 3-和 6-羟基。
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