Stereoselective synthesis of β-N-glycosides through 2-deoxy-2-nitroglycal

Shaohua Xiang; Jimei Ma; Bala Kishan Gorityala; Xue-Wei Liu

doi:10.1016/j.carres.2011.01.032

Stereoselective synthesis of β-N-glycosides through 2-deoxy-2-nitroglycal

Carbohydr Res. 2011 Dec 27;346(18):2957-9. doi: 10.1016/j.carres.2011.01.032. Epub 2011 Feb 4.

Authors

Shaohua Xiang¹, Jimei Ma, Bala Kishan Gorityala, Xue-Wei Liu

Affiliation

¹ Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

PMID: 22030462
DOI: 10.1016/j.carres.2011.01.032

Abstract

An efficient, base-free protocol has been developed for the β-stereoselective synthesis of N-glycosides from 2-nitroglycal and secondary amines. Simple protection and deprotection manipulations on the N-glycosides pave a way for the synthesis of biologically significant1,2-diaminosugars and glycopeptides.

Publication types

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

MeSH terms

Crystallography, X-Ray
Glucosamine / analogs & derivatives*
Glucosamine / chemistry
Glycosides / chemical synthesis*
Glycosides / chemistry*
Models, Molecular
Molecular Structure
Stereoisomerism

Substances

Glycosides
Glucosamine