Title:
NOVEL METHOD FOR SYNTHESIS OF INTERMEDIATE IN SYNTHESIS OF CARBAPENEM USING SUGAR TEMPLATE
Document Type and Number:
WIPO Patent Application WO/2007/013592
Kind Code:
A1
Abstract:
Disclosed is a method for producing an intermediate in the synthesis of a useful carbapenem anti-bacterial agent with good efficiency, more specifically the method described above which enables the introduction of a methyl group into position 1 of the carbapenem skeleton in a highly stereoselective manner and does not need the use of any expensive asymmetric auxiliary group, any catalyst that may cause an ultra-low temperature reaction or have any toxicity to a human body or the like and can recover the auxiliary group. In this method, a sugar template containing a propionate unit represented by the formula (II) is reacted with an acetoxyazetidinone represented by the formula (III) to form a carbon-carbon bond between them, thereby introducing a methyl group into position 1 of the carbapenem skeleton in the desired β-stereoselective manner.
Inventors:
TADANO KINICHI (JP)
TAKAO KENICHI (JP)
OKUE MASAYUKI (JP)
SUMI SHINJIRO (JP)
AJITO KEIICHI (JP)
TAKAO KENICHI (JP)
OKUE MASAYUKI (JP)
SUMI SHINJIRO (JP)
AJITO KEIICHI (JP)
Application Number:
PCT/JP2006/314992
Publication Date:
February 01, 2007
Filing Date:
July 28, 2006
Export Citation:
Assignee:
MEIJI SEIKA KAISHA (JP)
TADANO KINICHI (JP)
TAKAO KENICHI (JP)
OKUE MASAYUKI (JP)
SUMI SHINJIRO (JP)
AJITO KEIICHI (JP)
TADANO KINICHI (JP)
TAKAO KENICHI (JP)
OKUE MASAYUKI (JP)
SUMI SHINJIRO (JP)
AJITO KEIICHI (JP)
International Classes:
C07H13/02; C07D205/08
Domestic Patent References:
| WO1993013064A1 | 1993-07-08 |
Other References:
TOTANI K. ET AL.: "Highly stereoselective alfa-alkylations, 1,4-additions, and one-pot 1,4-addition/alfa-methylations achieved on 4-O-acyl and 4-O-crotonyl derivatives of methyl 6-deoxy-2,3-di-O-(t-butyldimethylsilyl)-alfa-Dglucopyranoside", SYNLETT, no. 11, 2001, pages 1772 - 1776, XP003006582
NAGATSUKA T. ET AL.: "Highly Diastereoselective Diels-Alder Reactions of Acrylic Esters Incorporated into A variety of Hexopyranosides", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 20, no. 7/8, 2001, pages 519 - 535, XP003005143
TOTANI K. ET AL.: "Highly Stereoselective 1,4-Conjugate Addition of Organocopper Reagents to Methyl alfa-D-Glucopyranoside Derivatives Tethering an Unsaturated Ester Moiety at C-4 or C-6", ORGANIC LETTERS, vol. 1, no. 9, 1999, pages 1447 - 1450, XP003006583
NAGATSUKA T. ET AL.: "Highly Diastereoselective Diels-Alder Reactions of Acrylic Esters Incorporated into A variety of Hexopyranosides", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 20, no. 7/8, 2001, pages 519 - 535, XP003005143
TOTANI K. ET AL.: "Highly Stereoselective 1,4-Conjugate Addition of Organocopper Reagents to Methyl alfa-D-Glucopyranoside Derivatives Tethering an Unsaturated Ester Moiety at C-4 or C-6", ORGANIC LETTERS, vol. 1, no. 9, 1999, pages 1447 - 1450, XP003006583
Attorney, Agent or Firm:
YOSHITAKE, Kenji et al. (Room 323 Fuji Bldg., 2-3, Marunouchi 3-chom, Chiyoda-ku Tokyo 05, JP)
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