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Synthesis of 2-deoxy-4-O-α- and -β-d-mannopyransyl-l-erythro-pentonic acids

✍ Scribed by Patricia Szabó; Ladislas Szabó

Publisher: Elsevier Science
Year: 1992
Tongue: English
Weight: 711 KB
Volume: 216
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(92)84164-n

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✦ Synopsis

The title compounds, required for the identification of structural features of the Bordetella pertussis endotoxin, have been synthesised by condensation of benzyl 3-O-benzyl-2-deoxy-beta-L-erythro-pentopyranoside with 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl bromide and with 4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl bromide, respectively, thus affording the fully protected alpha- and beta-linked disaccharides 7 and 12. Hypoiodite oxidation of the reducing disaccharides 9 and 14, obtained by conventional deprotection of 7 and 12, yielded the title compounds.

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