388570-21-6

Upstream product

• 97321-70-5 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-β-D-manno-hept-1-enitol 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 38184-10-0 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside 
• 82598-88-7 2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone 

Downstream Products

• 1192412-21-7 (5R,7R,8R,9S,10S)-8,9,10-tribenzyloxy-7-benzyloxymethyl-1-methoxycarbonyl-3,6-dioxa-2-thia-1-aza-spiro[4.5]decane-2,2-dioxide 
• 1192412-20-6 (5S,7R,8R,9S,10S)-8,9,10-tribenzyloxy-7-benzyloxymethyl-1-methoxycarbonyl-3,6-dioxa-2-thia-1-aza-spiro[4.5]decane-2,2-dioxide 
• 388570-22-7 3,4,5,7-tetra-O-benzyl-α-D-manno-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-α-D-manno-hept-2'-ulopyranose 1,2':2,1'-dianhydride 

Relevant academic research and scientific papers

Highly efficient synthesis of ketoheptoses

A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.

Regioselective synthesis and biological evaluation of spiro-sulfamidate glycosides from exo-glycals

We report the synthesis of spiro-sulfamidate glycosides from exo-glycals. This route is regioselective and furnishes an original class of spiro-hydantoin glycoside analogues. A biological evaluation of this family on a range of glycosidases shows that these compounds are weak but very selective inhibitors of α-glucosidase and amyloglucosidase.

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.