Rp-Diastereoselective synthesis of dinucleoside methylphosphonates by the phosphoramidite approach

In order to obtain diastereomeric control in the azole catalyzed coupling reaction of methylphosphonamidites, 2-(2′,4′,6′-trimethylbiphenyl-2-yl)-4,5-dicyanoimidazole 2 was synthesized. With its use as activator Rp-diastereoselective synthesis of dinucleoside methylphosphonates could be achieved for...

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Bibliographic Details
Published inTetrahedron letters Vol. 39; no. 47; pp. 8629 - 8632
Main Authors Schell, Peter, Engels, Joachim W.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.11.1998
Elsevier
Subjects
Chemistry
Chemistry, Organic
diastereoselection
imidazoles
nucleic acid analogues
phosphonamidites
Physical Sciences
Science & Technology
diastereoselection
imidazoles
nucleic acid analogues
phosphonamidites
CONTACTS
PHOSPHORUS
2'-DEOXY
ACID
STEREOCHEMISTRY
(3',5')-METHYLPHOSPHONATES
OLIGONUCLEOTIDES
phosphoramidites
LINKAGES
CHIRALITY
BACKBONE
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Summary:In order to obtain diastereomeric control in the azole catalyzed coupling reaction of methylphosphonamidites, 2-(2′,4′,6′-trimethylbiphenyl-2-yl)-4,5-dicyanoimidazole 2 was synthesized. With its use as activator Rp-diastereoselective synthesis of dinucleoside methylphosphonates could be achieved for the first time by the phosphoramidite approach. Selectivities were up to 84 16 (Rp/Sp). The mechanism of the reaction is based on dynamic kinetic resolution. With 2-(2′,4′,6′-trimethylbiphenyl-2-yl)-4,5-dicyanoimidazole 2 as activator the first directed synthesis of Rp-configurated methylphosphonates could be achieved.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)01972-8