The stereospecific synthesis of P-chiral biophosphates and their analogues by the Stec reaction

This manuscript summarizes the results of studies on the application of the reaction of dialkyl (aryl) phosphoramidate anions with carbonyl electrophiles for stereospecific synthesis of P-chiral biophosphates (Stec reaction). Following the results obtained with organic phosphoramidates which delinea...

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Bibliographic Details
Published in:Chemical Society reviews 2003-05, Vol.32 (3), p.158-169
Main Authors: Wozniak, Lucyna A, Okruszek, Andrzej
Format: Article
Language:English
Subjects:
Amides - chemistry
Chemistry, Organic - methods
Nucleotides - chemistry
Organophosphates - chemical synthesis
Organophosphates - chemistry
Phosphoric Acids - chemistry
Stereoisomerism
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Summary:This manuscript summarizes the results of studies on the application of the reaction of dialkyl (aryl) phosphoramidate anions with carbonyl electrophiles for stereospecific synthesis of P-chiral biophosphates (Stec reaction). Following the results obtained with organic phosphoramidates which delineated the scope of the reaction and its stereochemical course, the application of the title reaction is presented for the preparation of diastereomerically pure P-chiral cyclic nucleotide analogues (phosphorothioates, phosphoroselenoates, phosphoroselenothioates, isotopomeric 18O-phosphates), and P-chiral nucleoside monophosphate analogues, as well as dinucleoside phosphate analogues (phosphorothioates, methanephosphonates).
ISSN:0306-0012
1460-4744
DOI:10.1039/b207207f