Download PDF
Synthesis 1993; 1993(9): 889-894
DOI: 10.1055/s-1993-25964
paper
© 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.

Bromination of 1,5-Anhydrohex-1-enitols (Glycals) Using Quaternary Ammonium Tribromides as Bromine Donors: Synthesis of α-1,2-trans-2-Bromo-2-deoxyglycopyranosyl Bromides and Fluorides

Marcus Teichmann* , Gérard Descotes, Dominique Lafont
  • *Laboratoire de Chimie Organique 2, URA CNRS 463, Université Lyon I, ESCIL, 43 Bd du 11 Novembre 1918, F-69622-Villeurbanne Cedex, France
Further Information

Publication History

Publication Date:
29 April 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Addition of bromine to glycals using quaternary ammonium tribromides as bromine donors is realized with higher stereoselectivities (α-1,2-trans configurated products) compared to bromination with molecular bromine. The reaction is neither sensitive to the solvent nor to the nature of the protecting groups (acetyl, benzoyl, benzyl) of the glycals and very slightly affected by the orientation of the substituents of the different glycals. Some of the α-1, 2-trans dibromo adducts have been isolated in 60-75% yields and transformed into the corresponding α-1,2-trans-2-bromo-2-deoxyglycopyranosyl fluorides.