An olefin metathesis route for the preparation of (1-->6)-linked C-disaccharide glycals. A convergent and flexible approach to C-saccharide synthesis.
A convergent route to a variety of C-1-disaccharide glycals based on the olefin metathesis reaction of enol ethers and alkenes is described. The DCC-mediated coupling reaction of a variety of pentose enitols (1a-c) with a number of C-5- and C-6-monosaccharide carboxylic acids (2a-e) gave the corresponding esters 3a-l in good yield. Methylenation of these compounds was followed by ring-closing metathesis, mediated by the Schrock molybdenum catalyst 8 in warm toluene, to provide the target C-disaccharide glycals 5a-l. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.
Postema
M H
MH
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA. mpostema@chem.wayne.edu
Calimente
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D
Liu
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L
Behrmann
T L
TL
D000475:Alkenes / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002384:Catalysis; D002855:Chromatography, Thin Layer; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D008982:Molybdenum; D013056:Spectrophotometry, Ultraviolet
D000475:Alkenes; D004187:Disaccharides; D008982:Molybdenum