Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00532067" target="_blank" >RIV/61388963:_____/20:00532067 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22330/20:43920326

Výsledek na webu

<a href="https://doi.org/10.1016/j.carres.2020.108086" target="_blank" >https://doi.org/10.1016/j.carres.2020.108086</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.carres.2020.108086" target="_blank" >10.1016/j.carres.2020.108086</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals

Popis výsledku v původním jazyce

A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehydrochlorination reactions were studied on a range of glycosyl chlorides to provide suitable reaction conditions for this transformation. Benzyl ether, isopropylidene and benzylidene protecting groups, as well as interglycosidic linkage, were found to be compatible with this protocol. The described method is operationally simple and allows for the quick preparation of 2-hydroxyglycals with other than ester protecting groups, providing a feasible alternative to existing methods.

Název v anglickém jazyce

Straightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals

Popis výsledku anglicky

A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehydrochlorination reactions were studied on a range of glycosyl chlorides to provide suitable reaction conditions for this transformation. Benzyl ether, isopropylidene and benzylidene protecting groups, as well as interglycosidic linkage, were found to be compatible with this protocol. The described method is operationally simple and allows for the quick preparation of 2-hydroxyglycals with other than ester protecting groups, providing a feasible alternative to existing methods.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2020

Kód důvěrnosti údajů

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

Název periodika

Carbohydrate Research

ISSN

0008-6215

e-ISSN

—

Svazek periodika

496

Číslo periodika v rámci svazku

Oct

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

9

Strana od-do

108086

Kód UT WoS článku

000571835100009

EID výsledku v databázi Scopus

2-s2.0-85089520426