Synthesis of propyl and 2-aminoethyl glycosides of alpha-D-galactosyl-(1-->3')-beta-lactoside.
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.
Yudina
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ON
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119992 B-334, Moscow, Russia.
Sherman
A A
AA
Nifantiev
N E
NE
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*
C435776:2-aminoethyl-galactopyranosyl-(1-3')-lactoside; D000606:Amino Sugars; D006027:Glycosides; D007202:Indicators and Reagents; D013862:Thiogalactosides; D014312:Trisaccharides