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Medium‐Controlled Intramolecular Catalysis in the Direct Synthesis of 5′‐O‐Protected Ribonucleoside 2′‐ and 3′‐Dialkylphosphates
Author(s) -
Roussev Christo D.,
Ivanova Gabriela D.,
Bratovanova Emilia K.,
Petkov Dimiter D.
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(20000218)39:4<779::aid-anie779>3.0.co;2-j
Subject(s) - vicinal , intramolecular force , ribonucleoside , chemistry , electrophile , nucleophile , catalysis , aqueous solution , aqueous medium , solvent , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , rna , biochemistry , gene
Electrophilic participation of the cis ‐vicinal hydroxyl group accelerates the synthesis of the title compounds (see scheme). The aprotic, organic solvent induces a hydrogen‐bonded intermediate, thus providing a different phosphoryl transfer mechanism to the nucleophilic pathway observed in aqueous media.