Expedient Route to Chalcogenophosphinates with Glucose Moieties via Todd-Atherton-Like Coupling between Secondary Phosphine Chalcogenides and Diacetone-d-Glucose in the CCl4/Et3N System

ABSTRACT Secondary phosphine chalcogenides react with diacetone‐d‐glucose (DAG) in the system CCl4/Et3N (70°C, 4–24 h) to afford DAG chalcogenophosphinates in up to 79% yield, thus paving a short way to optically active chalcogenophosphinates with glucose moieties. As an example, a mild regioselecti...

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Published inHeteroatom chemistry Vol. 26; no. 5; pp. 329 - 334
Main Authors Volkov, Pavel А., Ivanova, Nina I., Gusarova, Nina K., Sukhov, Boris G., Khrapova, Kseniya O., Zelenkov, Lev E., Smirnov, Vladimir I., Borodina, Tatyana N., Vakul'skaya, Tamara I., Khutsishvili, Spartak S., Trofimov, Boris A.
Format Journal Article
LanguageEnglish
Published London Blackwell Publishing Ltd 01.09.2015
Hindawi Limited
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Summary:ABSTRACT Secondary phosphine chalcogenides react with diacetone‐d‐glucose (DAG) in the system CCl4/Et3N (70°C, 4–24 h) to afford DAG chalcogenophosphinates in up to 79% yield, thus paving a short way to optically active chalcogenophosphinates with glucose moieties. As an example, a mild regioselective hydrolysis (70°C, aqueous MeCOOH) of DAG bis(2‐phenylethyl)selenophosphinate) obtained leads to monoacetone‐d‐glucose bis(2‐phenylethyl)selenophosphinate.
Bibliography:ark:/67375/WNG-WFG5PTBQ-L
ArticleID:HC21264
istex:1441A0A100E58BD58E6B6B61F050BBC060A077FF
President of the Russian Federation - No. NSh-156.2014.3
Contract grant sponsor: President of the Russian Federation.Contract grant number: NSh‐156.2014.3.
ISSN:1042-7163
1098-1071
DOI:10.1002/hc.21264