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Convergent preparation of 1,6-linked C-disaccharides via olefin metathesis

✍ Scribed by Maarten H.D. Postema; Daniel Calimente

Book ID: 104261598
Publisher: Elsevier Science
Year: 1999
Tongue: French
Weight: 281 KB
Volume: 40
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(99)00815-1

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✦ Synopsis

The DCC mediated coupling reaction of 3,4,6-tri-O-benzyl-l,2-dideoxy-D-arabino-hex-l-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 and exposure to the Schrock molybdenum catalyst 1 in warm toluene, in the box, gave the target C-disaccharide glycals 9a-d in good yield. The 1,6-1inked gluco based C-disaccharide glycal 9a was converted to the 2-deoxy-f3-gluco-derivative 10a and the corresponding and gluco ~-gluco-C-disaccharide

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