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Carbohydr Res. 1987 Sep 15;167:197-210.

Total synthesis of X hapten, III3 Fuc alpha-nLc4 Cer.

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  • 1RIKEN Institute of Physical and Chemical Research, Saitama, Japan.

Abstract

Total synthesis of O-beta-D-galactopyranosyl-(1----4)-O-[alpha-L- fucopyranosyl- (1----3)]-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta- D- galactopyranosyl- (1----4)-O-beta-D-glucopyranosyl-(1----1)-2-N-tetracosanoyl-(2S,3R ,4E)- sphingenine was achieved by use of the key glycosyl donors O-(2,3,4,6-tetra-O-acetyl-beta-D- galactopyranosyl)-(1----4)-O-[(2,3,4-tri-O-acetyl-alpha-L-fucopyranosyl) - (1----3)]-O-(2- acetamido-6-O-acetyl-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-(2,4,6-tr i-O- acetyl- beta-D-galactopyranosyl)-(1----4)-2,3,6-tri-O-acetyl-alpha-D-glucopyrano syl trichloroacetimidate and fluoride, as well as key glycosyl acceptor 3-O-benzoyl-2-N-tetracosanoyl- (2S,3R,4E)-sphingenine, in an unambiguous manner.

PMID:
2891443
[PubMed - indexed for MEDLINE]
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