Download PDF
Synlett 1992; 1992(5): 413-414
DOI: 10.1055/s-1992-21363
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.

Two Syntheses of 3-Azido-3-deoxy-D-mannose

E. Wolfgang Holla* , Volker Sinnwell, Werner Klaffke
  • *Hoechst AG, Hauptlaboratorium G 830, D-6230 Frankfurt 80, Germany
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α-D-mannopyranose (10) was prepared from 1,6:3,4-dianhydro-β-D-altropyranose (8) by a nucelophilic oxirane-ring opening promoted by azide ions followed by acetolysis. Alternatively, regioselective enzymatic de-O-acetylation of 1,6-anhydro-2,4-di-O-acetyl..3-azido-3-deoxy-β-D-glucopyranose (1) gave isomers 2 and 3. The latter was reacted with trifluoromethanesulfonic acid anhydride/sodium acetate to give 1,6-anhydro-2,4-di-O-acetyl-3-azido-3-deoxy- β-D-mannopyranose (9).

      >