328386-14-7Relevant academic research and scientific papers
Synthesis of a C-disaccharide analog of the Thomsen-Friedenreich (T) epitope
Zhu,Vogel
, p. 79 - 81 (2007/10/03)
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 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-glycero-L- manno-heptitol-1-C-yl}-2-[(N-benzoxyl-N-benzyl)amino]-2,3 -dideoxy-1-thio-β-D-galacto-hexopyranoside (14).
