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Synlett 1998; 1998(5): 501-503
DOI: 10.1055/s-1998-1689
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Convenient Synthesis of α- and β-2-Deoxyglycosides

Julio C. Castro-Palomino* , Richard R. Schmidt
  • *Fakultät Chemie, Universität Konstanz, Fach M 725, D-78457 Konstanz, Germany; Fax + 49/7531/88 31 35
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Publication Date:
31 December 2000 (online)

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Readily available O-(2-O-thiobenzoyl-mannopyranosyl)trichloroacetimidate 4a gave with glucosides 7 and 8 as glycosyl acceptors exclusively α-linked disaccharides 9 α and 10 α. Accordingly, from O-(2-O-thiobenzoyl-glucopyranosyl)trichloroacetimidate 4b exclusively β-linked disaccharides 9 β and 10 β were obtained. Radical initiated deoxygenation with Bu3SnH/AIBN directly furnished 2-deoxyglycosides 11 α,β and 12 α,β.

2-deoxyglycosides - glycosidation - neighboring group participation - thiocarbonyloxy group - deoxygenation