Phosphorylated Glycoconjugates Based on Isosteviol, d-Arabinofuranose, and d-Ribofuranose

Autor:	I. Yu. Strobykina, Mayya G Belenok, Vladimir E. Kataev, R. R. Sharipova
Rok vydání:	2019
Předmět:	chemistry.chemical_classification Anomer 010405 organic chemistry Chemistry Stereochemistry Glycoconjugate Organic Chemistry Carbohydrate 01 natural sciences Terpenoid 0104 chemical sciences Dibutyl phosphate Ester bond Phosphorylation
Zdroj:	Russian Journal of Organic Chemistry. 55:508-513
ISSN:	1608-3393 1070-4280
DOI:	10.1134/s1070428019040158
Popis:	First phosphorylated glycoconjugates were synthesized in three stages on the basis of isosteviol, d-arabinofuranose, and d-ribofuranose. In the first stage, isosteviol reacted with methyl 5-O-(p-tosyl)-2,3-di-O-benzoyl-d-ribofuranoside and methyl 5-O-(p-tosyl)-2,3-di-O-benzoyl-d-arabinofuranoside to give glycoconjugates in which the diterpenoid fragment is linked through ester bond to the carbohydrate C5 atom. In the second stage, the anomeric methoxy group in the furanoside fragment was replaced by bromine, and the resulting 2,3-di-O-benzoyl-d-ribofuranosyl and 2,3-di-O-benzoyl-d-arabinofuranosyl bromides were treated with dibutyl phosphate to afford the target phosphorylated derivatives.
Databáze:	OpenAIRE
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