Synlett 1998; 1998(5): 501-503
DOI: 10.1055/s-1998-1689
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

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.

    >