Download PDF
Synlett 1996; 1996(3): 281-282
DOI: 10.1055/s-1996-5372
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.

Stereoselective Synthesis of α-C-Galactopyranosides of Conduritols and Aminoconduritols

Rafael Ferritto, Pierre Vogel*
  • *Section de Chimie de l’Université, BCH-Dorigny, 1015 Lausanne, Switzerland
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Giese’s radical glycosidation of (-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-oxybicyclo[2.2.1]-heptan-2-one with tetra-O-acetylbromo-α-D-galactopyranose gave a C-galactoside that was converted into (+)-(1S,2R,3S,4R)-6-chloro-3-endo-[(2’,3’,4’,6’-tetra-O-acetyl-α-D-galactopyranosyl)methyl]-7-oxabicyclo[2.2.1]hept-5-en-2-endo-yl acetate ((+)-6). Treatment of (+)-6 with HBr, then with LiN3 and subsequent reduction afforded (3S,4R,5R,6S)-3-amino-1-chloro-4-[(α-D-galactopyranosyl)methyl]-cyclohex-1-en-5,6-diol ((+)-10). Acidic hydrolysis of (+)-6 provided the (3R,4R,5R,6S)-1-chloro-4-[(α-D-galactopyranosyl)methyl]-cyclohex-1-en-3,5,6-triol derivative (+)-11 or the (4R,5R,6S)-4-[(α-D-galactopyranosyl)methyl]-5,6-dihydroxycyclohex-2-en-1-one derivative (-)-12 selectively.

C-Glycosides - disaccharide mimics - 7-oxabicyclo[2.2.1]hept-2-enes - ”naked sugar” - 1-chlorocyclohex-2-enyl cations

      >