Synthesis of Neplanocin A Analog with 2′-“up”-C-Methyl Substituent as Potential Anti-HCV Agent 


Vol. 30,  No. 9, pp. 2043-2050, Sep.  2009
10.5012/bkcs.2009.30.9.2043


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  Abstract

2′-β-C-Methylneplanocin A (3) was synthesized via 2-β-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 N2 product 27 along with an N2′ product 28.

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  Cite this article

[IEEE Style]

H. R. Lee, J. A. Kang, A. Y. Park, W. H. Kim, P. Chun, J. Kim, J. A. Kim, B. Lee, L. S. Jeong, H. R. Moon, "Synthesis of Neplanocin A Analog with 2′-“up”-C-Methyl Substituent as Potential Anti-HCV Agent," Bulletin of the Korean Chemical Society, vol. 30, no. 9, pp. 2043-2050, 2009. DOI: 10.5012/bkcs.2009.30.9.2043.

[ACM Style]

Hyung Rock Lee, Jin Ah Kang, Ah Young Park, Won Hee Kim, Pusoon Chun, Jungsu Kim, Jin Ah Kim, Boeun Lee, Lak Shin Jeong, and Hyung Ryong Moon. 2009. Synthesis of Neplanocin A Analog with 2′-“up”-C-Methyl Substituent as Potential Anti-HCV Agent. Bulletin of the Korean Chemical Society, 30, 9, (2009), 2043-2050. DOI: 10.5012/bkcs.2009.30.9.2043.

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ISSN(Print) 0253-2964
ISSN(Online) 1229-5949