142573-75-9Relevant academic research and scientific papers
A practical synthesis of xylo- and arabinofuranoside precursors by diastereoselective reduction using Corey-Bakshi-Shibata catalyst
Utley, Lynn M.,Maldonado, Jessica,Awad, Ahmed M.
, p. 20 - 34 (2018/02/06)
The Corey-Bakshi-Shibata (CBS) catalyst provides an efficient mechanism to reduce ketones and achieve desired enantiopure alcohols. Herein, the diastereoselective reduction of C-2′ and C-3′-keto ribofuranoside derivatives to the corresponding arabino- and xylofuranosides in greater than 95% diastereomeric excess is reported. The stereo-directed substitution with an azido group as well as the synthesis of prodrugs cytarabine and vidarabine are also described. The reported strategy offers superior diastereoselectivity, shorter reaction times, and obviates cooling required with comparable protocols involving achiral reductants.
Synthesis of 2'-deuterio and 3'-deuterio cytidine 5'-diphosphate.
Sandbrink, Jessica,Stroemberg, Roger
, p. 1657 - 1659 (2007/10/03)
2'-2H- and 3'-2H-CDP were synthesized from 5'-MMT-3'-O-TBDMS and 2',5'-O-diTBDMS cytidine derivatives, respectively, by oxidation followed by acidic removal of 5'-protection, reduction with [NaBD(OAc)3] and finally displacement of a tosyl group by pyropho
The S,X-acetals in nucleoside chemistry: II. The synthesis of 3′-O-methylthiomethylribonucleosides
Pechenov,Zavgorodny,Shvets,Miroshnikov
, p. 407 - 413 (2007/10/03)
3′-O-Methylthiomethyl derivatives of ribonucleosides were synthesized from the selectively protected nucleosides by the action of a dimethyl sulfide-benzoyl peroxide mixture in acetonitrile or a dimethyl sulfoxide-acetic anhydride-acetic acid mixture.
