title: Synthesis of propyl and 2-aminoethyl glycosides of alpha-D-galactosyl-(1-->3')-beta-lactoside.
abstract: Propyl and 2-aminoethyl alpha-D-galactopyranosyl-(1-->3')-beta-lactosides (1 and 2) were prepared from the corresponding perbenzylated trisaccharide allyl glycoside 6 which, in turn, was obtained by methyl triflate promoted alpha-galactosylation of benzylated allyl lactoside acceptor 4 with thiogalactoside 3. Transformation of the allyl moiety in compound 6 into 2-azidoethyl one was achieved by cleavage of the double bond followed by reduction into alcohol 9, subsequent mesylation, and mesylate-->azide substitution. Alternatively trisaccharide 2 was synthesized using alpha-galactosylation of selectively benzoylated 2-azidoethyl lactoside 19 with 3 as the key step.
authors: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119992 B-334, Moscow, Russia.
authors: O N
authors: ON
authors: Yudina
authors: A A
authors: AA
authors: Sherman
authors: N E
authors: NE
authors: Nifantiev
mesh_terms: D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009904:Optical Rotation; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013862:Thiogalactosides; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C435776:2-aminoethyl-galactopyranosyl-(1-3')-lactoside; D000606:Amino Sugars; D006027:Glycosides; D007202:Indicators and Reagents; D013862:Thiogalactosides; D014312:Trisaccharides