1. ChemInform Abstract: Stereoselective Koenigs-Knorr Glycosylation Catalyzed by Urea
- Author
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Xiaowei Wu, Lifeng Sun, Xin-Shan Ye, and De-Cai Xiong
- Subjects
animal structures ,Glycosylation ,Anomer ,Stereochemistry ,fungi ,macromolecular substances ,General Medicine ,Catalysis ,carbohydrates (lipids) ,chemistry.chemical_compound ,chemistry ,Urea ,lipids (amino acids, peptides, and proteins) ,Stereoselectivity ,Glycosyl ,Selectivity ,Phosphine - Abstract
A stereoselective Koenigs-Knorr glycosylation reaction under the catalysis of urea is described. This method is characterized by urea-mediated hydrogen-bond activation and subsequent glycosylation with glycosyl chlorides or bromides. Excellent yields and high anomeric selectivity can be achieved in most cases. Moreover, the low α-stereoselectivity of glycosylations observed when using perbenzylated glucosyl donors can be greatly improved by the addition of tri-(2,4,6-trimethoxyphenyl)phosphine (TTMPP).
- Published
- 2016