489432-84-0Relevant academic research and scientific papers
Straightforward synthesis of diverse 1-deoxyazapyranosides via stereocontrolled nucleophilic additions to six-membered cyclic nitrones
Chan, Ting-Hao,Chang, Yi-Fan,Hsu, Jung-Jung,Cheng, Wei-Chieh
supporting information; experimental part, p. 5555 - 5559 (2011/01/05)
A systematic study of diastereoselective nucleophilic addition of Grignard reagents to six-membered chiral tri-O-benzyl cyclic nitrones is described. With all eight chiral cyclic nitrones and asymmetric reaction conditions in hand, a practical methodology is established for the preparation of diverse 1-deoxyazapyranosides bearing various stereogenic centers. We have developed practical methods to prepare all eight six-membered chiral cyclic nitrones. Using these cyclic nitrones and diastereoselective nucleophilic additions, 12 examples of diverse 1-deoxyazapyranosides including enantiomers were synthesized to demonstrate the generality and flexibility of this new approach.
TBAT-mediated nitrone formation of ω-mesyloxy-O-tert-butyldiphenylsilyloximes: Facile synthesis of cyclic nitrones from hemiacetals
Tamura, Osamu,Toyao, Atsushi,Ishibashi, Hiroyuki
, p. 1344 - 1346 (2007/10/03)
Chiral and cyclic nitrones were synthesized by TBAT-mediated desilylative cyclization of ω-mesyloxy-O-tert-butyl-diphenylsilyloximes, readily prepared from sugar derivatives by a consecutive treatment with O-tert-butyldiphenylsilylhydroxylamine and with m
