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Oligosaccharides from “standardized intermediates”. The 2-amino-2-deoxy-d-galactose analog of the blood-group O(H) determinant, type 2, and its precursors

✍ Scribed by Mina A. Nashed; Laurens Anderson

Publisher: Elsevier Science
Year: 1983
Tongue: English
Weight: 598 KB
Volume: 114
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(83)88172-5

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✦ Synopsis

The selectively benzylated glycoside allyl 2-acetamido-4,6-di-O-benzyl-2-deoxy-beta-D-galactopranoside (4) was prepared from the corresponding derivative of 2-acetamido-2-deoxy-D-glucose via the p-bromobenzenesulfonate and the benzoate. 2-O-Benzoyl-3,4,6-tri-O-benzyl-alpha-D-galactopyranosyl (10) was obtained from allyl 6-O-benzyl-2-O-(2-butenyl)-alpha-D-galactopyranoside via known intermediates. To complete the sequence, the 1-propenyl 3,4,6-tri-O-benzyl galactoside was successively converted into the 2-benzoate, the free sugar, and the chloride 10. A fully protected form (11) of the trisaccharide alpha-L-Fucp-(1 leads to 2)-beta-D-Galp-(1 leads to 4)-D-GalNAc was then synthesized by coupling 10 to 4, partially deblocking the disaccharide product, and L-fucosylating the resulting intermediate. Cleavage of the O-benzyl groups from 11, with concomitant saturation of the allyl group, gave the propyl beta-glycoside of the unsubstituted trisaccharide.

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