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Start Over Author "Nifantiev, N. E." Journal carbohydrate research
5 results on '"Nifantiev, N. E."'

5. Synthesis of propyl and 2-aminoethyl glycosides of alpha-D-galactosyl-(1-->3')-beta-lactoside.

Author

Yudina ON, Sherman AA, and Nifantiev NE

Subjects
Carbohydrate Conformation, Carbohydrate Sequence, Indicators and Reagents, Models, Molecular, Molecular Sequence Data, Optical Rotation, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization, Thiogalactosides, Amino Sugars chemical synthesis, Amino Sugars chemistry, Glycosides chemical synthesis, Glycosides chemistry, Trisaccharides chemical synthesis, Trisaccharides chemistry
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.

Published
2001
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