First synthesis of a branched beta-C-tetrasaccharide using a triple ring closing metathesis cyclization.
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.
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA.
Jared L
JL
Piper
Maarten H D
MH
Postema
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D003500:Cyclization; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*
D009844:Oligosaccharides