First synthesis of a branched beta-C-tetrasaccharide using a triple ring closing metathesis cyclization

Jared L Piper; Maarten H D Postema

doi:10.1021/jo040203w

First synthesis of a branched beta-C-tetrasaccharide using a triple ring closing metathesis cyclization

J Org Chem. 2004 Oct 15;69(21):7395-8. doi: 10.1021/jo040203w.

Authors

Jared L Piper¹, Maarten H D Postema

Affiliation

¹ Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA.

PMID: 15471503
DOI: 10.1021/jo040203w

Abstract

The first synthesis of a branched beta-C-tetrasaccharide has been carried out through the use of an esterification-ring closing metathesis (RCM) strategy. The precursor triacid 2a was readily prepared via standard chemical methods from a known starting material, and dehydrative coupling with an excess of olefin alcohol 1a gave triester 3a in excellent yield. Methylenation of the triester 3a and subsequent triple RCM reaction was followed by an in situ hydroboration-oxidation to furnish the branched beta-C-tetrasaccharide 6a in good overall yield.

Publication types

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

MeSH terms

Carbohydrate Conformation
Carbohydrate Sequence
Cyclization
Molecular Sequence Data
Oligosaccharides / chemical synthesis*

Substances

Oligosaccharides