78879-95-5Relevant academic research and scientific papers
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)
Takamura, Tsukasa,Chiba, Taku,Tejima, Setsuzo
, p. 1076 - 1082 (2007/10/02)
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
CHEMICAL MODIFICATION OF LACTOSE. XIV. SYNTHESIS OF O-2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL-(1-3)-O--O-β-D-GALACTOPYRANOSYL-(1-4)-β-D-GLUCOPYRANOSE (3',6'-DI-β-N-ACETYLGLUCOSAMINYL-β-LACTOSE)
Takamura, Tsukasa,Chiba, Taku,Tejima, Setsuzo
, p. 1027 - 1033 (2007/10/02)
The title branched tetrasaccharide (18) is the core structure of more complex oligosaccharides of human milk.A synthesis of 18 was achieved.Stirring of the acetylated oxazoline derivative of GlcNAc (6 mol eq.), 1,6-anhydro-2,2',3,4'-tetra-O-benzyl-β-galac
