Synthesis of 2'-O-substituted ribonucleosides.
An efficient synthesis of 2'-O-substituted ribonucleosides, including 2'-O-TBDMS and 2'-O-TOM protected as well as 2'-O-Me and 2'-O-allyl derivatives is presented. Di-t-butylsilylene group was employed for simultaneous protection of 3'- and 5'- hydroxyl functions of nucleoside on the first step. Subsequent silylation or alkylation of free 2'-OH followed by introduction of suitable protection on the base moiety and removal of cyclic silyl protection gave target compounds in a high yield.
Serebryany
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Ribozyme Pharmaceuticals Inc., Boulder, Colorado 80301, USA. serebru@rpi.com
Beigelman
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D000478:Alkylation; D007202:Indicators and Reagents; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D017646:Organosilicon Compounds; D012263:Ribonucleosides / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D007202:Indicators and Reagents; D017646:Organosilicon Compounds; D012263:Ribonucleosides; C404749:tert-butyldimethylsilyl chloride