232603-07-5Relevant articles and documents
Convergent preparation of 1,6-linked C-disaccharides via olefin metathesis
Postema, Maarten H. D.,Calimente, Daniel
, p. 4755 - 4759 (1999)
The DCC mediated coupling reaction of 3,4,6-tri-O-benzyl-1,2-dideoxy-D- arabino-hex-1-enitol (5a) with a variety of sugar based carboxylic acids 6a- d gave esters 7a-d in good yield. Methylenation of the formed esters led to the acyclic enol ethers 8a-d a
An olefin metathesis route for the preparation of (1 → 6)-linked C-disaccharide glycals. A convergent and flexible approach to C-saccharide synthesis
Postema, Maarten H. D.,Calimente, Daniel,Liu, Lei,Behrmann, Tonja L.
, p. 6061 - 6068 (2007/10/03)
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-1 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-1. The formed enol ether double bond in 5a was then transformed, via standard manipulations, into a variety of C-disaccharide derivatives 21-25.