82845-97-4Relevant articles and documents
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)
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.
The preparation of protected arabinonucleosides
Ogilvie, Kelvin K.,McGee, Danny P. C.,Boisvert, Suzanne M.,Hakimelahi, Gholam H.,Proba, Zbigniew A.
, p. 1204 - 1212 (2007/10/02)
A general procedure is described for the preparation of protected arabinonucleosides.Protection at the 5'-position involves triphenylmethyl groups (DMT and MMT) while the tert-butyldimethylsilyl (TBDMS) group is used to protect the 2'- or 3'-positions.The
