Title:
METHOD FOR SYNTHESIZING CHIRAL 2-HYDROXY-1,4-DICARBONYL COMPOUND AND PANTOLACTONE
Document Type and Number:
WIPO Patent Application WO/2020/220651
Kind Code:
A1
Abstract:
Disclosed are a method for synthesizing a chiral 2-hydroxy-1,4-dicarbonyl compound by using a tetrapeptide TP or an enantiomer ent-TP thereof as a chiral catalyst to catalyze an asymmetric Aldol reaction between fatty aldehyde and glyoxylate or between fatty aldehyde and acyl formaldehyde monohydrate, and a use of a synthetic product. The method for synthesizing a chiral 2-hydroxy-1,4-dicarbonyl compound by using an asymmetric Aldol reaction is shown in formulas 1 and 2. An optically active 2-hydroxy-1,4-dicarbonyl compound is synthesized by catalyzing an asymmetric Aldol reaction between fatty aldehyde and glyoxylate, and an optically active pantolactone or an analog thereof may further be synthesized according to the foregoing. The present invention has the advantages of reaction conditions being mild, operation being easy, the amount of a catalyst being little, being able to use tetrapeptide and an enantiomer thereof to synthesize 2-hydroxy-1,4-dicarbonyl compounds of two configurations, and yield being high.
Inventors:
DA CHAOSHAN (CN)
DU ZHIHONG (CN)
TAO BAOXIU (CN)
QIN WENJUAN (CN)
YUAN MENG (CN)
BAI YANBING (CN)
LIN XING (CN)
ZHANG LIANCHUN (CN)
YIN HANGHUA (CN)
JIANG WEILIN (CN)
YU JIANXIN (CN)
LIU XUEYU (CN)
JIN WENJIU (CN)
DU ZHIHONG (CN)
TAO BAOXIU (CN)
QIN WENJUAN (CN)
YUAN MENG (CN)
BAI YANBING (CN)
LIN XING (CN)
ZHANG LIANCHUN (CN)
YIN HANGHUA (CN)
JIANG WEILIN (CN)
YU JIANXIN (CN)
LIU XUEYU (CN)
JIN WENJIU (CN)
Application Number:
PCT/CN2019/119629
Publication Date:
November 05, 2020
Filing Date:
November 20, 2019
Export Citation:
Assignee:
UNIV LANZHOU (CN)
HANGZHOU XINFU SCIENCE & TECH CO LTD (CN)
HANGZHOU XINFU SCIENCE & TECH CO LTD (CN)
International Classes:
C07C67/343; C07C69/675; C07D307/33
Foreign References:
| CN102985400A | 2013-03-20 | |||
| CN201910352646A | 2019-04-29 |
Other References:
MARCEL HEIDLINDEMANN, ET AL.: "Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 80, 28 February 2015 (2015-02-28), pages 3387 - 3396, XP055495038, DOI: 20200211150110Y
MARCEL HEIDLINDEMANN, ET AL.: "Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 80, 28 February 2015 (2015-02-28), pages 3387 - 3396, XP055495038, DOI: 20200211132740A
WU, FENGCHUN ET AL.: "N-Primary-Amine-Terminal β-Turn Tetrapeptides as Organocatalysts for Highly Enantioselective Aldol Reaction", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 74, 21 May 2009 (2009-05-21), pages 4812 - 4818, XP055750716, DOI: 20200211133014Y
WANG, JINJIN ET AL.: "Progress in the Asymmetric Synthesis of Chiral Pantolactone", INDUSTRIAL CATALYSIS, vol. 22, no. 5, 31 May 2014 (2014-05-31), pages 335 - 340, XP055861760
LAM YU-HONG, ET AL.: "Stereoselectivities of Histidine-Catalyzed Asymmetric Aldol Additions and Contrasts with Proline Catalysis: A Quantum Mechanical Analysis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 134, 31 March 2012 (2012-03-31), pages 6286 - 6295, XP055495037, DOI: 20200211132521A
DAVIE, E. A. C.MENNEN, S. M.XU, YMILLER, S. J., CHEM. REV., vol. 107, 2007, pages 5759 - 5812
ZHONG, G.FAN, J.BARBAS, C. F., TETRAHEDRON LETT, vol. 45, 2004, pages 5681 - 5684
MARKERT, M.SCHEFFLER, U.MAHRWALD, R., J. AM. CHEM. SOC., vol. 131, 2009, pages 16642 - 16643
ROHR, K.MAHRWALD, R., ORG. LETT., vol. 14, 2012, pages 2180 - 2183
HEIDLINDEMANN, M.HAMMEL, M.SCHEFFLER, U.MAHRWALD, R.HUMMEL, W.BERKESSEL, A.GROGER, H., J. ORG. CHEM., vol. 80, 2015, pages 3387 - 3396
KANO, T.MARUOKA K., ANGEW. CHEM. INT. ED., vol. 46, 2007, pages 1738 - 1740
KANO, T.MARUOKA, K., CHEM. EUR. J., vol. 15, 2009, pages 6678 - 6687
YAN X.FENG, X. M., SYNLETT, 2008, pages 73 - 76
MARCEL HEIDLINDEMANN, ET AL.: "Chemoenzymatic Synthesis of Vitamin B5-Intermediate (R)-Pantolactone via Combined Asymmetric Organo- and Biocatalysis", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 80, 28 February 2015 (2015-02-28), pages 3387 - 3396, XP055495038, DOI: 20200211132740A
WU, FENGCHUN ET AL.: "N-Primary-Amine-Terminal β-Turn Tetrapeptides as Organocatalysts for Highly Enantioselective Aldol Reaction", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 74, 21 May 2009 (2009-05-21), pages 4812 - 4818, XP055750716, DOI: 20200211133014Y
WANG, JINJIN ET AL.: "Progress in the Asymmetric Synthesis of Chiral Pantolactone", INDUSTRIAL CATALYSIS, vol. 22, no. 5, 31 May 2014 (2014-05-31), pages 335 - 340, XP055861760
LAM YU-HONG, ET AL.: "Stereoselectivities of Histidine-Catalyzed Asymmetric Aldol Additions and Contrasts with Proline Catalysis: A Quantum Mechanical Analysis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 134, 31 March 2012 (2012-03-31), pages 6286 - 6295, XP055495037, DOI: 20200211132521A
DAVIE, E. A. C.MENNEN, S. M.XU, YMILLER, S. J., CHEM. REV., vol. 107, 2007, pages 5759 - 5812
ZHONG, G.FAN, J.BARBAS, C. F., TETRAHEDRON LETT, vol. 45, 2004, pages 5681 - 5684
MARKERT, M.SCHEFFLER, U.MAHRWALD, R., J. AM. CHEM. SOC., vol. 131, 2009, pages 16642 - 16643
ROHR, K.MAHRWALD, R., ORG. LETT., vol. 14, 2012, pages 2180 - 2183
HEIDLINDEMANN, M.HAMMEL, M.SCHEFFLER, U.MAHRWALD, R.HUMMEL, W.BERKESSEL, A.GROGER, H., J. ORG. CHEM., vol. 80, 2015, pages 3387 - 3396
KANO, T.MARUOKA K., ANGEW. CHEM. INT. ED., vol. 46, 2007, pages 1738 - 1740
KANO, T.MARUOKA, K., CHEM. EUR. J., vol. 15, 2009, pages 6678 - 6687
YAN X.FENG, X. M., SYNLETT, 2008, pages 73 - 76
Attorney, Agent or Firm:
UNITALEN ATTORNEYS AT LAW (CN)
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