Formation of beta-glucosamine and beta-mannose linkages using glycosyl phosphates

O J Plante; E R Palmacci; P H Seeberger

doi:10.1021/ol006566+

Formation of beta-glucosamine and beta-mannose linkages using glycosyl phosphates

Org Lett. 2000 Nov 30;2(24):3841-3. doi: 10.1021/ol006566+.

Authors

O J Plante¹, E R Palmacci, P H Seeberger

Affiliation

¹ Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

PMID: 11101433
DOI: 10.1021/ol006566+

Abstract

[reaction: see text] Glycosyl phosphates were examined for their utility in the synthesis of challenging glycosidic linkages. beta-Glucosamine glycosides were formed preferentially and in good yield. beta-Mannosides were constructed in high overall yield with modest anomeric selectivity. Interesting solvent and conformational influences on the stereochemical outcome of the coupling reactions were observed.

Publication types

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

MeSH terms

Acetonitriles
Glucosamine / chemistry*
Glycosides / chemical synthesis*
Glycosylation
Indicators and Reagents
Magnetic Resonance Spectroscopy
Mannose / chemistry*
Mannosides / chemical synthesis
Molecular Conformation
Organophosphates / chemistry*

Substances

Acetonitriles
Glycosides
Indicators and Reagents
Mannosides
Organophosphates
Glucosamine
Mannose
acetonitrile