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Synlett 2001; 2001(1): 0079-0081
DOI: 10.1055/s-2001-9698
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Synthesis of a C-Disaccharide Analog of the Thomsen-Friedenreich (T) Epitope

Yao-Hua Zhu* , Pierre Vogel
  • *Section de Chimie de l'Université, BCH, CH-1015 Lausanne-Dorigny, Switzerland; Fax +41 21 692 3975; E-mail: pierre.vogel@ico.unil.ch
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Publication Date:
31 December 2001 (online)

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The 2,3,4,6-tetra-O-[(tert-butyl)dimethylsilyl]-C-β-d-galactopyranosylformaldehyde (2,6-anhydro-1,3,4,6-tetra-O-[(tert-butyl)dimethylsilyl]-d-glycero-l-manno-heptose, 2) was condensed with isolevoglucosenone (3) in the presence of Et2AlI 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-β-d-glycero-hex-2-enopyranos-4-ulose (8). Diastereoselective conjugate addition of BnONHBn to 8, followed b 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-glycero-l-manno-heptitol-1-C-yl]-2-[(N-benzoxyl-N-benzyl)amino]-2,3-dideoxy-1-thio-β-d-galacto-hexopyranoside (14).

Baylis-Hillman reaction with Et2AlI - C-disaccharide - epitope T - C-β-d-dalactopyranosylformaldehyde - isolevoglucosenone - non-hydrolyzable epitope analog