A novel approach to functionalization of allyl aglycon. Effective synthesis of selectively protected 2-aminoethyl lactoside, a common building block for the synthesis of carbohydrate chains of glycolipids

Autor:	P. E. Cheshev, Leonid O. Kononov, Nikolay E. Nifant'ev
Rok vydání:	2000
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Glycolipid Ozonolysis chemistry Double bond Stereochemistry Glycoside Amine gas treating Sequence (biology) General Chemistry Oxime Aldehyde
Zdroj:	Russian Chemical Bulletin. 49:1305-1309
ISSN:	1573-9171 1066-5285
Popis:	A novel approach to the functionalization of aglycon in allyl glycosides is described. The method comprises ozonolysis of the double bond in the allyl group, leading to the corresponding aldehyde, and subsequent transformation of the latter into the corresponding oxime, which is finally reduced to give the amine. The efficiency of this synthetic sequence (yield ∼90%) is exemplified by the transformation of two allyl lactoside derivatives into selectively protected 2-aminoethyl lactosides. The latter are convenient common building blocks for the synthesis of carbohydrate chains of glycolipids that have a lactose unit at the reducing end.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::656649ef6efd064eaa700f374fa7c5c5 https://doi.org/10.1007/bf02495780 Zobrazit plný text záznamu Full text from SpringerLink