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Synthesis of Neplanocin A Analog with 2′-“up”-C-Methyl Substituent as Potential Anti-HCV Agent
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  • Synthesis of Neplanocin A Analog with 2′-“up”-C-Methyl Substituent as Potential Anti-HCV Agent
  • Synthesis of Neplanocin A Analog with 2′-“up”-C-Methyl Substituent as Potential Anti-HCV Agent
저자명
Lee. Hyung-Rock,Kang. Jin-Ah,Park. Ah-Young,Kim. Won-Hee,Chun. Pu-Soon,Kim. Jung-Su,Kim. Jin-Ah,Lee. Bo-Eun,Jeong. Lak-Shin,Moon
간행물명
Bulletin of the Korean Chemical Society
권/호정보
2009년|30권 9호|pp.2043-2050 (8 pages)
발행정보
대한화학회
파일정보
정기간행물|ENG|
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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기타언어초록

2′-$eta$-C-Methylneplanocin A (3) was synthesized via 2-$eta$-C-methylribonolactone, prepared by a modified Whistler and BeMiller’s method developed by our laboratory, as potential anti-HCV agent. Reduction of 14 with Dibal-H afforded 26 in a good yield with a trace of 25, whereas a Luche reduction gave 26/25 = 4/1 mixture. Several attempts were made to chemoselectively remove TBS group in the presence of TBDPS group and treatment with both PPTS and TsOH showed the best result. Condensation of 26 with 6-chloropurine under Mitsunobu conditions produced an $S_N$2 product 27 along with an $S_N$2′ product 28.