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Synlett 1996; 1996(3): 281-282
DOI: 10.1055/s-1996-5372
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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
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Publication History

Publication Date:
31 December 2000 (online)

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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