180187-77-3Relevant academic research and scientific papers
Enantiomeric Synthesis of L-(or 1′R,2′S)-Carbocyclic Cyclopropyl Nucleosides
Lee, Mi Gyoung,Du, Jin Fa,Chun, Moon Woon,Chu, Chung K.
, p. 1991 - 1995 (1997)
The enantiomeric synthesis of carbocyclic cyclopropyl L-nucleosides has been accomplished from L-gulonic γ-lactone. The key intermediate 3 was stereoselectively synthesized by DIBAL-H reduction and silyl protection followed by cyclopropanation from ester 2, which was in turn prepared from L-gulonic γ-lactone (1) in five steps. Desilylation of cyclopropyl intermediate 3 gave alcohol 4, which was then converted to the urea derivative 5 and cyclopropylamine 7 by Curtius rearrangement of an acyl azide. The urea intermediate 5 was utilized to prepare thymine 10, uracil 11, and cytosine 14 derivatives. The hypoxanthine, adenine, and guanine nucleosides 21, 22, and 24 were synthesized from the amino intermediate 7.
Enantioselective Synthesis of Cyclopropyl Carbocyclic L-Nucleosides
Lee, Migyoung,Lee, Doowon,Zhao, Yufen,Newton, M. Gary,Chun, Moon Woo,Chu, Chung K.
, p. 3499 - 3502 (1995)
Enantioselective synthesis of pyrimidine and purine cyclopropyl carbocyclic L-nucleosides has been accomplished from L-gulono-γ-lactone and the X-ray structure of the key intermediate 9,(1R,2S,4'R)-2-(2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropyl urea, has b
