Synthesis of Neplanocin A Analog with 2¡Ç-¡°up¡±-C-Methyl Substituent as Potential Anti-HCV Agent

Bulletin of the Korean chemical society

Hyung Rock Lee¹  Ah Young Park¹  Jungsu Kim¹  Lak Shin Jeong¹  Pusoon Chun¹  Won Hee Kim¹  Boeun Lee¹  Jin Ah Kang¹  Hyung Ryong Moon¹  Jin Ah Kim¹ 

关键词: 2¡Ç-¥â-C-Methylneplanocin A;    2-¥â-C-Methylribonolactone;    Chemoselective;    HCV;    PDC oxidation;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

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 SN2 product 27 along with an SN2�? product 28.

【 授权许可】

Unknown