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  4. Synthesis of α-D-(1→3) and α-D-(1→4)-C-linked galactosides of D-mannose derivatives. Conformation of α-C-galactosides
 
research article

Synthesis of α-D-(1→3) and α-D-(1→4)-C-linked galactosides of D-mannose derivatives. Conformation of α-C-galactosides

Ferritto, R.
•
Vogel, P.  
1994
Tetrahedron-Asymmetry

Reductive radical alpha-D-galactosidation of 5-exo-(benzeneselenyl)-6-endo-chloro-3-methylidene-7- -oxabicyclo[2.2.1]heptan-2-one with acetobromo-D-galactose, followed by ketone reduction led to (+)-(1R,2S, 3R,4S,5S,6S)-5-exo-(benzeneselenyl)-6-endo-chloro-3-endo-[(2',3',4',6'-t etra-O-acetyl-alpha-D-galactopyranosyl)me- thyl]-7-oxabicyclo[2.2.1]heptan-2-endo-ol which was converted into (+)-methyl 3-deoxy-3-[(alpha-D-galactopyranosyl)methyl]-alpha-D-mannopyranoside (1), (+)-3-deoxy-3-[alpha-D-galactopyranosyl)methyl]-D-mannitol (2) and 4-deoxy-4-[(2',3',4',6'-tetra-O-acetyl-alpha-D-galactopyranosyl)methyl]- 2,3,6-tri-O-acetyl-D-mannono-1,5-lactone (3). H-1-MNR data of the alpha-C-galactosides confirmed that their preferred conformations involve antiperiplanar arrangements for the C-linked substrates and bond sigma C(1'),C(2') of the alpha-(1-->3)-C-galactoside unit. The alpha-(1-->3)-C-galactoside of methyl mannopyranoside 1 adopts a conformation similar to that proposed for methyl 3-O-(alpha-D-galactopyranosyl)-alpha-D-mannopyranoside.

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Type
research article
DOI
10.1016/S0957-4166(00)86285-0
Author(s)
Ferritto, R.
Vogel, P.  
Date Issued

1994

Published in
Tetrahedron-Asymmetry
Volume

5

Issue

11

Start page

2077

End page

2092

Subjects

D-glycopyranosyl phenylsulfones

•

preferred conformation

•

syncytium

•

formation

•

vinyl carbanions

•

bond formation

•

disaccharides

•

glycosides

•

inhibitors

•

chemistry

•

additions

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/20.500.14299/219690
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