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  4. Synthesis of a C-disaccharide analog of the Thomsen-Friedenreich (T) epitope
 
research article

Synthesis of a C-disaccharide analog of the Thomsen-Friedenreich (T) epitope

Zhu, Y. H.
•
Vogel, P.  
2001
Synlett

The 2,3,4,6-tetra-O-[(tert-butyl)dimethylsilyl]-C-beta -D- galactopyranosylformaldehyde (2,6-anhydro-1,3,4,6-tetra-O-[(tert-butyl)dimethylsilyl]-D-glycero-L-man no-heptose, 2) was condensed with isolevoglucosenone (3) in the presene e of Et(2)AII to give 1,6-anhydro-3-C- {(1R)-2,6-anhydro-3,4,5,7-tetra-O-[(tert-butyl)dimethylsilyl]-D-glycero- L-manno-heptitol-1-C-yl}-2,3-dideoxy-beta -D-glycero-hex-2-enopyranos-4-ulose (8). Diastereoselective conjugate addition of BnONHBn to 8, followed by diastereoselective ketone reduction with LiBH4 and treatment with Me3SiSPh/ZnI2, provided phenyl 3-C-{(1R)-2,6-anhydro-3,4,5,7-tetra-O[(tert-butyl)dimethylsilyl]-D-glyce ro-L-manno-heptitol-1-C-yl}-2-[ (N-benzoxyl-N-benzyl)amino]-2,3-dideoxy-1-thio-beta -D-galacto-hexopyranoside (14).

  • Details
  • Metrics
Type
research article
DOI
10.1055/s-2001-9698
Author(s)
Zhu, Y. H.
Vogel, P.  
Date Issued

2001

Published in
Synlett
Issue

1

Start page

79

End page

81

Subjects

Baylis-Hillman reaction with Et2AlI

•

C-disaccharide

•

epitope T

•

C-beta-D-galactopyranosylformaldehyde

•

isolevoglucosenone

•

non-hydrolyzable epitope

•

Active specific immunotherapy

•

altered glycosylation

•

carcinoma

•

cancer

•

glycoproteins

•

antigens

•

carbohydrate

•

derivatives

•

glycosides

Note

Univ Lausanne, BCH, 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/20.500.14299/219791
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