Synthesis of propyl and 2-aminoethyl glycosides of alpha-D-galactosyl-(1-->3')-beta-lactoside. |
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Authors: | O N Yudina A A Sherman N E Nifantiev |
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Institution: | N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119992 B-334, Moscow, Russia. |
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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. |
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