Additive-controlled stereoselective glycosylations of 2,3-oxazolidinone protected glucosamine or galactosamine thioglycoside donors with phenols based on preactivation protocol

Qi Qin; De-Cai Xiong; Xin-Shan Ye

doi:10.1016/j.carres.2014.07.004

Additive-controlled stereoselective glycosylations of 2,3-oxazolidinone protected glucosamine or galactosamine thioglycoside donors with phenols based on preactivation protocol

Carbohydr Res. 2015 Feb 11:403:104-14. doi: 10.1016/j.carres.2014.07.004. Epub 2014 Jul 17.

Authors

Qi Qin¹, De-Cai Xiong¹, Xin-Shan Ye²

Affiliations

¹ State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing 100191, China.
² State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing 100191, China. Electronic address: [email protected].

PMID: 25108483
DOI: 10.1016/j.carres.2014.07.004

Abstract

Stereo-controllable glycosylation reactions of 2,3-oxazolidinone protected glucosamine thioglycoside donor with different phenol acceptors based on preactivation protocol, are described. It was found that BF3·Et2O worked as α-directing additive, while TTBP acted as β-directing additive. Simply by altering additives, either α-aryl glycosides or β-aryl glycosides were achieved in a stereoselective manner. The additives were also applied to the stereoselective glycosylation reactions of 2,3-oxazolidinone protected galactosamine donor with phenol substrates.

Keywords: Additive; Aryl glycoside; Glycosylation; Preactivation; Stereoselectivity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Galactosamine / chemistry*
Glucosamine / chemistry*
Glycosylation
Oxazolidinones / chemistry*
Phenols / chemistry*
Stereoisomerism
Substrate Specificity
Thioglycosides / chemistry*

Substances

Oxazolidinones
Phenols
Thioglycosides
Galactosamine
Glucosamine