Synthesis of methyl 3-O- and 2-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-alpha D-galactopyranoside. 1983

S A Abbas, and K L Matta

Condensation of methyl 2-O-benzoyl-4,6-O-benzylidene-alpha-D-galactopyranoside with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl bromide (1) in dichloromethane, in the presence of silver trifluoromethanesulfonate, 2,4,6-trimethylpyridine, and molecular sieves, afforded methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalim ido- beta-D-glucopyranosyl)-alpha-D-galactopyranoside (4). Deacetalation of 4 in hot, 80% aqueous acetic acid gave methyl 2-O-benzoyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido- beta-D-glucopyranosyl)-alpha-D-galactopyranoside (5), which, on deacylation, followed by peracetylation, furnished the peracetylated disaccharide derivative (6). The structures of 5 and 6 were established by 1H-n.m.r. spectroscopy. O-Deacetylation of 6 afforded the title beta-(1 leads to 3)-linked disaccharide 7. For the synthesis of the beta-(1 leads to 2)-linked isomer, methyl 3-O-benzoyl-4,6-O-benzylidene-alpha-D-galactopyranoside was similarly condensed with bromide 1 to give the fully protected disaccharide derivative (8). Cleavage of the benzylidene group of 8 gave methyl 3-O-benzoyl-2-O-(3,4,6- tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-alpha-D- galactopyranoside (9). Deacetylation of 9, followed by peracetylation, afforded the peracetate (10). O-Deacetylation of 10 gave the beta-(1 leads to 2)-linked disaccharide (11). The structures of the disaccharides 7 and 11 were confirmed by 13C-n.m.r. spectroscopy.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D008895 Milk, Human Milk that is produced by HUMAN MAMMARY GLANDS. Breast Milk,Human Milk,Milk, Breast
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009844 Oligosaccharides Carbohydrates consisting of between two (DISACCHARIDES) and ten MONOSACCHARIDES connected by either an alpha- or beta-glycosidic link. They are found throughout nature in both the free and bound form. Oligosaccharide
D011247 Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH. Gestation,Pregnancies
D001789 Blood Group Antigens Sets of cell surface antigens located on BLOOD CELLS. They are usually membrane GLYCOPROTEINS or GLYCOLIPIDS that are antigenically distinguished by their carbohydrate moieties. Blood Group,Blood Group Antigen,Blood Groups,Antigen, Blood Group,Antigens, Blood Group,Group Antigen, Blood,Group, Blood,Groups, Blood
D002236 Carbohydrate Conformation The characteristic 3-dimensional shape of a carbohydrate. Carbohydrate Linkage,Carbohydrate Conformations,Carbohydrate Linkages,Conformation, Carbohydrate,Conformations, Carbohydrate,Linkage, Carbohydrate,Linkages, Carbohydrate
D004187 Disaccharides Oligosaccharides containing two monosaccharide units linked by a glycosidic bond. Disaccharide
D005260 Female Females
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man

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