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Practical synthesis of a potent hepatitis C virus RNA replication inhibitor. 2004
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. matthew_bio@merck.com
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.
Related Publications
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
September 2006,
Chembiochem : a European journal of chemical biology,
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
April 2010,
Archives of virology,
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
January 2013,
Current topics in microbiology and immunology,
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
August 2005,
Journal of medicinal chemistry,
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
February 2006,
The Journal of biological chemistry,
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
January 2006,
Antiviral chemistry & chemotherapy,
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
June 2004,
Virus research,
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
May 2003,
The Journal of biological chemistry,
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
March 2006,
Gastroenterology,
Matthew M Bio, and
Feng Xu, and
Marjorie Waters, and
J Michael Williams, and
Kimberly A Savary, and
Cameron J Cowden, and
Chunhua Yang, and
Elizabeth Buck, and
Zhiguo J Song, and
David M Tschaen, and
R P Volante, and
Robert A Reamer, and
Edward J J Grabowski
June 2009,
Antimicrobial agents and chemotherapy,
