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Method of determining absolute configuration of chiral compound

Foreign code F110005276
File No. E04703US
Posted date Aug 29, 2011
Country United States of America
Application number 14865200
Gazette No. 20030008406
Gazette No. 7354771
Date of filing Dec 4, 2000
Gazette Date Jan 9, 2003
Gazette Date Apr 8, 2008
International application number JP2000008559
International publication number WO2001040774
Date of international filing Dec 4, 2000
Date of international publication Jun 7, 2001
Priority data
  • P1999-345538 (Dec 3, 1999) JP
  • 2000WO-JP08559 (Dec 4, 2000) WO
Title Method of determining absolute configuration of chiral compound
Abstract (US7354771)
The absolute configuration of a chiral compound is determined by (i) coordinating the chiral compound to a metalloporphyrin having a carbon chain-crosslinked porphyrin dimer structure in which one of the two porphyrin rings has at least one ethyl or substituent bulkier than ethyl at at least one of the second peripheral carbon atoms from the carbon atom at the carbon chain crosslink site, and (ii) analyzing the resultant coordination compound by circular dichroism spectrophotometry to determine the absolute configuration of the asymmetric carbon based on the sign of the Cotton effect.
The chiral compound has an asymmetric carbon bonded to a basic group capable of coordinating to the metal of the other porphyrin ring of the metalloporphyrin dimer or an asymmetric carbon atom adjacent to the carbon atom bonded to the basic group.
Scope of claims [claim1]
1. A method for determining the absolute configuration of a chiral compound which comprises: coordinating the chiral compound to a metalloporphyrin represented by the following formula (I):
{mu {{5,5'- (ethane-1, 2-diyl) bis [2, 3, 7, 8, 12, 13, 17, 18-octaethyl-21H, 23H-porphyrinato](4-)}-kappa N21, -kappa N22, -kappa N23, -kappa N24, -kappa N21', -kappa N22', -kappa N23', -kappa N24', }}dizinc,
the chiral compound having an asymmetric carbon bonded to a basic group capable of coordinating to the metal of the other porphyrin ring of the metalloporphyrin dimer or an asymmetric carbon atom adjacent to the carbon atom bonded to the basic group;
and analyzing the resultant coordination compound by circular dichroism spectrophotometry to determine the absolute configuration of the asymmetric carbon of the chiral compound based on the sign of the Cotton effect, wherein when the first Cotton effect is positive, the absolute configuration of the chiral compound is (S), and when the first Cotton effect is negative, the absolute configuration of the chiral compound is (R).
[claim2]
2. The method according to claim 1 wherein the chiral compound is 1) a primary amine, 2) a secondary amine, 3) a primary diamine, 4) a secondary diamine, 5) a monoalcohal, or 6) an aminoalcohol.
  • Inventor, and Inventor/Applicant
  • INOUE YOSHIHISA
  • BOROVKOV VICTOR
  • LINTULUOTO JUHA
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
IPC(International Patent Classification)
Reference ( R and D project ) ERATO INOUE Photo-chirogenesis AREA
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