Title:
METHOD FOR PRODUCING (2R)-2-FLUORO-2-C-METHYL-D-RIBONO-Γ-LACTONE PRECURSOR
Document Type and Number:
WIPO Patent Application WO/2011/152155
Kind Code:
A1
Abstract:
Disclosed is a method for producing a (2R)-2-fluoro-2-C-methyl-D-ribono-γ-lactone precursor of an open-ring fluorinated compound [In the formula, Me represents a methyl group, R1 represents an alkyl group or an alkyl substituent, P1 and P2 respectively represent the protective group of a hydroxyl group, and X+ represents a proton or a protonated organic base.] by reacting 1,2-diols with an organic base, and with sulfuryl fluoride (SO2F2) in the presence of a fluoride ion source, if necessary. The aforementioned production method involves fewer number of steps compared to conventional production methods, and fulfills the requirements (high yield and excellent reproducibility) for an industrial production method. The (2R)-2-fluoro-2-C-methyl-D-ribono-γ-lactone precursor thus obtained can be used as the important intermediate of 2'-deoxy-2'-fluoro-2'-C-methylcytidine having anti-viral activity.
Inventors:
ISHII AKIHIRO
NAGURA HIROKATSU
TSURUTA HIDEYUKI
NAGURA HIROKATSU
TSURUTA HIDEYUKI
Application Number:
PCT/JP2011/060024
Publication Date:
December 08, 2011
Filing Date:
April 25, 2011
Export Citation:
Assignee:
CENTRAL GLASS CO LTD (JP)
ISHII AKIHIRO
NAGURA HIROKATSU
TSURUTA HIDEYUKI
ISHII AKIHIRO
NAGURA HIROKATSU
TSURUTA HIDEYUKI
International Classes:
C07D317/30; A61K31/7068; C07B61/00; C07H19/073
Domestic Patent References:
| WO2006031725A2 | 2006-03-23 | |||
| WO2008045419A1 | 2008-04-17 | |||
| WO2009075186A1 | 2009-06-18 | |||
| WO2009025169A1 | 2009-02-26 | |||
| WO2010047266A1 | 2010-04-29 | |||
| WO2008045419A1 | 2008-04-17 | |||
| WO2006031725A2 | 2006-03-23 | |||
| WO2006012440A2 | 2006-02-02 |
Foreign References:
| JP2006290870A | 2006-10-26 |
Other References:
WANG P. ET AL.: "An Efficient and Diastereoselective Synthesis of PSI-6130: A Clinically Efficacious Inhibitor of HCV NS5B Polymerase", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 74, no. 17, 2009, pages 6819 - 6824, XP055070592
L'HEUREUX A. ET AL.: "Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 10, 2010, pages 3401 - 3411, XP008158944
See also references of EP 2578578A4
J. ORG. CHEM. (US, vol. 74, 2009, pages 6819 - 6824
"Protective Groups in Organic Synthesis, Third Edition,", 1999, JOHN WILEY & SONS, INC.
L'HEUREUX A. ET AL.: "Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 75, no. 10, 2010, pages 3401 - 3411, XP008158944
See also references of EP 2578578A4
J. ORG. CHEM. (US, vol. 74, 2009, pages 6819 - 6824
"Protective Groups in Organic Synthesis, Third Edition,", 1999, JOHN WILEY & SONS, INC.
Attorney, Agent or Firm:
KOBAYASHI, Hiromichi et al. (JP)
Hiromichi Kobayashi (JP)
Hiromichi Kobayashi (JP)
Download PDF:
Claims:
Previous Patent: PANEL PROTECTION SHEET, PACKING BOX
Next Patent: STRUCTURE FOR MOUNTING ANTI-FOG SHEET TO VISOR SHIELD
Next Patent: STRUCTURE FOR MOUNTING ANTI-FOG SHEET TO VISOR SHIELD