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Synthesis of specifically deoxygenated disaccharide derivatives of the Shigella dysenteriae type 1 O-antigen

✍ Scribed by Laurence A. Mulard; Cornelis P.J. Claudemans

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 851 KB
Volume: 274
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(95)00122-a

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✦ Synopsis

The synthesis of methyl O-ot-L-rhamnopyranosyl-(1 ~ 2)-Ot-D-galactopyranosides specifically deoxygenated at position 2 (31), or 4 (21) of the rhamnopyranosyl residue was accomplished using methyl 3,4,6-tfi-O-benzoyl-a-D-galactopyranoside (15) as the glycosyl acceptor. Phenyl thionocarbonate activation of the penta-O-benzoylated disaccharide precursor followed by Barton reduction and Zempl6n transesterification gave 31, while 21 was obtained via condensation of the deoxygenated monosaccharide donor with 18, and subsequent debenzoylation of the product.

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