Synthesis and characterization of propyl O-beta-D-galactopyranosyl-(1----4)-O-beta-D-galactopyranosyl-(1----4)- alpha-D-galactopyranoside. 1984

H A El-Shenawy, and C Schuerch

Allyl 4-O-(4-O-acetyl-2-O-benzoyl-3,6-di-O-benzyl-beta-D-galactopyranosyl)- 2-O-benzoyl-3,6-di-O-benzyl-alpha-D-galactopyranoside was O-deallylated to give the 1-hydroxy derivative, and this was converted into the corresponding 1-O-(N-phenylcarbamoyl) derivative, treatment of which with dry HCl produced the alpha-D-galactopyranosyl chloride. This was converted into the corresponding 2,2,2-trifluoroethanesulfonate, which was coupled to allyl 2-O-benzoyl-3,6-di-O-benzyl-alpha-D-galactopyranoside, to give crystalline allyl 4-O-[4-O-(4-O-acetyl-2-O-benzoyl-3,6-di-O-benzyl- beta-D-galactopyranosyl)-2-O-benzoyl-3,6-di-O-benzyl-beta-D-galactopyran osyl]- 2-O-benzoyl-3,6-di-O-benzyl-alpha-D-galactopyranoside (15) in 85% yield, no trace of the alpha anomer being found. The trisaccharide derivative 15 was de-esterified with 2% KCN in 95% ethanol, and the product O-debenzylated with H2-Pd, to give the unprotected trisaccharide. Alternative sequences are discussed.

UI MeSH Term Description Entries
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
D014312 Trisaccharides Oligosaccharides containing three monosaccharide units linked by glycosidic bonds. Trisaccharide

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