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  4. Stereoselective synthesis of alpha-C-galactopyranosides of conduritols and aminoconduritols
 
research article

Stereoselective synthesis of alpha-C-galactopyranosides of conduritols and aminoconduritols

Ferritto, R.
•
Vogel, P.  
1996
Synlett

Giese's radical glycosidation of (-)-(1S,4R,5R,6R)-5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7-o xabicyclo[2.2.1]-heptan-2-one with tetra-O-acetylbromo-alpha-D-galactopyranose gave a C-galactoside that was converted into (+)-(1S,2R,3S,4R)-6-chloro-3,3-endo-[(2',3',4',6'-tetra-O-acetyl-alpha-D -galactopyranosyl)methyl]-7-oxa-bicyclo[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-[(alpha-D-galactopyranosyl)methyl]-cycl ohex-1-en-5,6-diol ((+)-10). Acidic hydrolysis of (+)-6 provided the (3R,4R,5R,6S)-1-chloro-4-[(alpha-D-galactopyranosyl)methyl]-cyclohex-hex -1-en-3,5,6-triol derivative (+)-11 or the (4R,5R,6S)-4-[(alpha-D-galactopyranosyl)methyl]-5,6-dihydroxycyclohex-2- en-1-one derivative (-)-12 selectively.

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Type
research article
DOI
10.1055/s-1996-5372
Author(s)
Ferritto, R.
Vogel, P.  
Date Issued

1996

Published in
Synlett
Issue

3

Start page

281

End page

282

Subjects

C-glycosides

•

disaccharide mimics

•

7-oxabicyclo[2.2.1]hept-2-enes

•

''naked sugar''

•

1-chlorocyclohex-2-enyl cations

•

Cell recognition

•

carba-sugars

•

disaccharides

•

derivatives

•

glycosides

•

additions

•

palytoxin

Note

Univ lausanne,bch dorigny,chim sect,ch-1015 lausanne,switzerland.

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
November 9, 2005
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/219714
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