One-pot synthesis of glucosamine oligosaccharides

Micha Fridman; Dmitry Solomon; Shay Yogev; Timor Baasov

doi:10.1021/ol017054d

One-pot synthesis of glucosamine oligosaccharides

Org Lett. 2002 Jan 24;4(2):281-3. doi: 10.1021/ol017054d.

Authors

Micha Fridman¹, Dmitry Solomon, Shay Yogev, Timor Baasov

Affiliation

¹ Department of Chemistry and Institute of Catalysis Science and Technology, Technion-Israel Institute of Technology, Haifa 32000, Israel.

PMID: 11796070
DOI: 10.1021/ol017054d

Abstract

[reaction: see text] Tuning the reactivity of glycosyl donors derived from 2-amino-2-deoxy glucose by selective introduction of different N-protecting (NPhth and NHTroc) and anomeric leaving groups (ethylthio and phenylthio) enabled highly efficient oligosaccharide synthesis in a one-pot manner. One-pot sequential glycosylation of three and four units of 2-amino-2-deoxy glucose gave trisaccharides and tetrasaccharide in 50-81% yields.

Publication types

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

MeSH terms

Glucosamine / chemical synthesis*
Glucosamine / chemistry
Oligosaccharides / chemical synthesis*
Thioglycosides / chemistry

Substances

Oligosaccharides
Thioglycosides
Glucosamine