Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F10%3A63509363" target="_blank" >RIV/70883521:28110/10:63509363 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Selective formation of glycosidic linkages of N-unsubstituted 4-hydroxyquinolin-2-(1H)-ones

Original language description

A comparative study for selective glucosylation of N-unsubstituted 4 hydroxyquinolin-2(1H)-ones into 4-(tetra-O-acetyl--D-glucopyranosyloxy)quinolin-2(1H)-ones is reported. Four glycosyl donors including tetra-O-acetyl--D-glucopyranosyl bromide, -D-glucose pentaacetate, glucose tetraacetate and tetra-O-acetyl--D-glucopyranosyl trichloroacetimidate were tested, along with different promoters and reaction conditions. The best results were obtained with tetra-O-acetyl--D-glucopyranosyl bromide with Cs2CO3in CH3CN. In some cases the 4-O-glucosylation of the quinolinone ring was accompanied by 2-O-glucosylation yielding the corresponding 2,4-bis(tetra-O-acetyl--D-glucopyranosyloxy)quinoline. Next, 4-(tetra-O-acetyl--D-glucopyranosyloxy)quinolin-2(1H)-oneswere deacetylated into 4-(-D-glucopyranosyloxy)quinolin-2(1H)-ones with Et3N in MeOH. In some instances the deacetylation was accompanied by the sugar?aglycone bond cleavage. Structure elucidation, complete assignment of proton and carbon

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2010

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Carbohydrate Research

ISSN

0008-6215

e-ISSN

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Volume of the periodical

345

Issue of the periodical within the volume

6

Country of publishing house

GB - UNITED KINGDOM

Number of pages

11

Pages from-to

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UT code for WoS article

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EID of the result in the Scopus database

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