388570-20-5

Basic information

• Product Name: 3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose
• Synonyms: 3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose
• CAS NO: 388570-20-5
• Molecular Weight: 570.683
• Mol File: 388570-20-5.mol

Chemical Properties

• CAS DataBase Reference: 3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose(388570-20-5)
• EPA Substance Registry System: 3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose(388570-20-5)

Safety Data

• Hazardous Substances Data: 388570-20-5(Hazardous Substances Data)

Upstream product

• 179090-11-0 (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one 
• 82598-84-3 2,3,4,6-tetra-O-benzyl-D-galactonolactone 

Downstream Products

• 394211-72-4 (2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-ol 
• 394212-00-1 2-((2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-ethanol 
• 394212-02-3 2-((2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-1-[(2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-ethanol 
• 394211-92-8 (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-carbaldehyde 
• 394211-94-0 (2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-carbaldehyde 
• 350484-72-9 3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-β-D-galacto-hept-2'-ulopyranose 1,2':2,1'-dianhydride 
• 350484-73-0 3,4,5,7-tetra-O-benzyl-α-D-galacto-hept-2-ulopyranose 3',4',5',7'-tetra-O-benzyl-α-D-galacto-hept-2'-ulopyranose 1,2':2,1'-dianhydride 

Relevant articles and documents

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.

α(1-3)-galactosyltransferase inhibition based on a new type of disubstrate analogue

How do retaining glycosyltransferases function? To answer this question, UDP-Gal and galactose were covalently linked to form disubstrate analogues 1, of which surprisingly 1β and not 1α inhibited α(1-3)-galactosyltransferases very well. An understanding