Practical synthesis of a potent hepatitis C virus RNA replication inhibitor.
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.
Bio
Matthew M
MM
Process Research, Merck Research Laboratories, P.O. Box 2000, Rahway, New Jersey 07065, USA. matthew_bio@merck.com
Xu
Feng
F
Waters
Marjorie
M
Williams
J Michael
JM
Savary
Kimberly A
KA
Cowden
Cameron J
CJ
Yang
Chunhua
C
Buck
Elizabeth
E
Song
Zhiguo J
ZJ
Tschaen
David M
DM
Volante
R P
RP
Reamer
Robert A
RA
Grabowski
Edward J J
EJ
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D016174:Hepacivirus / Q000235:genetics*; D009682:Magnetic Resonance Spectroscopy; D012367:RNA, Viral / Q000096:biosynthesis*
D000998:Antiviral Agents; D012367:RNA, Viral