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Efficient route to orthogonally protected precursors of 2-acylamino-2-deoxy-3-O-substituted-β-d-glucopyranose derivatives and use thereof

✍ Scribed by Julien Boutet; Tae Hee Kim; Catherine Guerreiro; Laurence A. Mulard

Book ID: 104095531
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 409 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.06.052

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✦ Synopsis

An efficient route to two 3-O-acyl-2-deoxy-4,6-O-isopropylidene-2-trichloroacetamido-D-glucopyranosyl trichloroacetimidate donors is reported. As demonstrated for the 3-O-acetyl derivative, these building blocks are exquisite b-D-glucosamine donors when reacted either with simple alcohols or with complex oligosaccharides. Besides, their protection pattern is compatible with selective deprotection and subsequent chain elongation at O-3 of the newly incorporated glucosamine residue.

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