78880-10-1

Basic information

• Product Name: O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-(1-3)-O-(2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1-4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose
• Synonyms: O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-(1-3)-O-(2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1-4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose
• CAS NO: 78880-10-1
• Molecular Weight: 955.022
• Mol File: 78880-10-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-(1-3)-O-(2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1-4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-(1-3)-O-(2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1-4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose(78880-10-1)
• EPA Substance Registry System: O-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-(1-3)-O-(2-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1-4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose(78880-10-1)

Safety Data

• Hazardous Substances Data: 78880-10-1(Hazardous Substances Data)

Upstream product

• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 78880-06-5 1,6-anhydro-2,2',3-tri-O-benzyl-4',6'-O-benzylidene-β-lactose 

Relevant articles and documents

CHEMICAL MODIFICATION OF LACTOSE. XV. SYNTHESES OF O-α- AND O-β-L-FUCOPYRANOSYL-(1->3)-O-β-D-GALACTOPYRANOSYL-(1->4)-D-GLUCOPYRANOSES (3'-O-α- AND 3'-O-β-L-FUCOPYRANOSYLLACTOSES)

1,6-Anhydro-4',6'-O-benzylidene-3'-O-tosyl-β-lactose was converted into 1,6-anhydro-2,2',3-tri-O-benzyl-4',6'-O-benzylidene-β-lactose (3) in 74.1percent yield by benzylation followed by detosylation.Condensation of 3 with 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide in benzene-nitromethane in the presence of mercuric cyanide and molecular sieves gave the corresponding trisaccharide derivatives (6 and 11) bearing α- and β-L-fucopyranosyl linkages in 37.1 and 43.1percent yields, respectively.Compounds 6 and 11 were isolated by column chromatography on silica gel.The title sugars (10 and 15) were prepared in 4 steps from 6 and 11, respectively; hydrogenolytic removal of the benzylidene and benzyl groups, acetylation, cleavage of the 1,6-anhydro-β-ring to β-acetate, and deacetylation. 1H-NMR and 13C-NMR spectral data of 10, 15, and the intermediates are also described.Keywords: synthesis; 3'-O-α-L-fucopyranosyllactose; 3'-O-β-L-fucopyranosyllactose; human milk oligosaccharide; glycosylation; lactosan derivatives; 1,6-anhydro-β-trisaccharide derivatives; 1H-NMR; 13C-NMR