350484-72-9

Upstream product

• 350484-59-2 4-Pentenyl 3,4,5,7-tetra-O-benzyl-α-D-galacto-heptulopyranoside 
• 179090-11-0 (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one 
• 388570-20-5 3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose 
• 350484-63-8 4-Pentenyl 3,4,5,7-tetra-O-benzyl-1-O-[3,4,5,7-tetra-O-benzyl-α-D-galacto-heptulopyranosyl]-α-D-galacto-heptulopyranoside 

Relevant academic research and scientific papers

Stereoselective synthesis and structure elucidation of spiro-ketodisaccharides

Cycloglycosylation of 3,4,5,7-tetra-O-benzyl-α-D-hept-2-ulopyranoses (2a-c) was carried out stereoselectively under the catalysis of Lewis acid to afford two spiro-cyclodisaccharides 3a-c and 4a-c in good yields. The reaction provided the kinetic products 3a-c or the thermodynamic products 4a-c as the predominant products under different conditions, respectively. The unprotected disaccharides 5a-c and 6a-c and the acetylated derivatives 7a-c and 8a-c were prepared by catalytic hydrogenation and followed by acetylation. The structures of compounds 4a-c, 6a-c and 8a-c were confirmed to be α,β-anomeric configuration with chair-chair-chair form for the tri-cycles based on the X-ray crystallographic analysis of 6a-c. The α,α-anomeric configurations of compounds 3a-c, 5a-c and 7a-c were determined based on the measurements of the three bond coupling constants 3JC,H between the C-1 and the H-3 of 7a-c.

Chemical synthesis of linear and cyclic unnatural oligosaccharides by iterative glycosidation of ketoses

The development of an efficient method for the stereoselective synthesis of α-D-(2 → 1)-linked ketoside oligomers is described. The method is based on an iterative protocol composed of two key steps: a) the coupling of a thiazolylketosyl phosphite donor w