179927-40-3Relevant 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.
A practical synthesis of sugar-derived cyclic nitrones: Powerful synthons for the synthesis of iminosugars
Wang, Wu-Bao,Huang, Mu-Hua,Li, Yi-Xian,Rui, Pei-Xin,Hu, Xiang-Guo,Zhang, Wei,Su, Jia-Kun,Zhang, Zhao-Lan,Zhu, Jian-She,Xu, Wei-Hua,Xie, Xian-Qing,Jia, Yue-Mei,Yu, Chu-Yi
experimental part, p. 488 - 492 (2010/04/26)
Sugar-derived cyclic nitrones were synthesized from the corresponding aldoses through an efficient and practical procedure involving a seven-step reaction sequence in good to excellent overall yield (10-42%). This synthetic strategy, requiring only inexpe
Exploratory experiments with aryl telluride carbohydrates. Synthesis of carbocycles using intramolecular radical cyclization
Barton, Derek H.R.,Gero, Stephane D.,Holliday, Pascale,Quiclet-Sire, Beatrice
, p. 8233 - 8244 (2007/10/03)
The preparation of cyclohexanoids and cyclopentanoids, potential precursors of biologically interesting molecules is described. The key step of the synthesis is an exo cyclization of 5-hexenyl or 6-heptenyl radicals. The radical, generated by radical exchange from carbohydrate anisyl tellurides (D-galactose or D-arabinose) cyclized into polyhydroxylated cyclohexane or cyclopentane derivatives.
