24667-52-5Relevant 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
SYNTHESIS OF O-α-L-FUCOPYRANOSYL-(1-->3)-O-β-D-GALACTOPYRANOSYL-(1-->4)-D-GLUCOSE (3'-O-α-L-FUCOPYRANOSYLLACTOSE), AND AN IMPROVED ROUTE TO ITS β-(1"-->3')-LINKED ISOMER
Baer, Hans H.,Abbas, Saeed A.
, p. 53 - 60 (2007/10/02)
Isopropylidenation of lactose with 2,2-dimethoxypropane in N,N-dimethylformamide at 80-85 degC gave a 1:2 mixture of the kinetically favored 4',6'-acetal 1 and the thermodynamically more-stable 3',4'-acetal 2, which were separated by chromatography.The 1,
