Literature DB >> 15357584

Practical synthesis of a potent hepatitis C virus RNA replication inhibitor.

Matthew M Bio1, Feng Xu, Marjorie Waters, J Michael Williams, Kimberly A Savary, Cameron J Cowden, Chunhua Yang, Elizabeth Buck, Zhiguo J Song, David M Tschaen, R P Volante, Robert A Reamer, Edward J J Grabowski.   

Abstract

A practical, efficient synthesis of 1, a hepatitis C virus RNA replication inhibitor, is described. Starting with the inexpensive diacetone glucose, the 12-step synthesis features a novel stereoselective rearrangement to prepare the key crystalline furanose diol intermediate. This is followed by a highly selective glycosidation to couple the C-2 branched furanose epoxide with deazapurine.

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Year:  2004        PMID: 15357584     DOI: 10.1021/jo0491096

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  Inhibition of dengue virus RNA synthesis by an adenosine nucleoside.

Authors:  Yen-Liang Chen; Zheng Yin; Jeyaraj Duraiswamy; Wouter Schul; Chin Chin Lim; Boping Liu; Hao Ying Xu; Min Qing; Andy Yip; Gang Wang; Wai Ling Chan; Hui Pen Tan; Melissa Lo; Sarah Liung; Ravinder Reddy Kondreddi; Ranga Rao; Helen Gu; Handan He; Thomas H Keller; Pei-Yong Shi
Journal:  Antimicrob Agents Chemother       Date:  2010-05-10       Impact factor: 5.191

2.  Synthesis of 7-trifluoromethyl-7-deazapurine ribonucleoside analogs and their monophosphate prodrugs.

Authors:  Jong Hyun Cho; Leda C Bassit; Franck Amblard; Raymond F Schinazi
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2019-10-07       Impact factor: 1.381

3.  Total synthesis of a marine alkaloid--rigidin E.

Authors:  Banpeng Cao; Haixin Ding; Ruchun Yang; Xiaoji Wang; Qiang Xiao
Journal:  Mar Drugs       Date:  2012-06-20       Impact factor: 6.085

4.  First total synthesis of a naturally occurring iodinated 5'-deoxyxylofuranosyl marine nucleoside.

Authors:  Jianyun Sun; Yanhui Dou; Haixin Ding; Ruchun Yang; Qi Sun; Qiang Xiao
Journal:  Mar Drugs       Date:  2012-04-10       Impact factor: 6.085

5.  1,2:5,6-Di-O-iso-propyl-idene-3-C-methyl-α-d-allo-furan-ose.

Authors:  Luana da Silva Magalhães Forezi; Marcos Moitrel Pequeno Silva; Fernanda da Costa Santos; Vitor Francisco Ferreira; Maria Cecília Bastos Vieira de Souza
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-09-07
  5 in total

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