Title:
METHOD FOR PRODUCING NEOPONKORANOL OR ANALOG THEREOF
Document Type and Number:
WIPO Patent Application WO/2011/093471
Kind Code:
A1
Abstract:
Provided is a method for producing neoponkoranol or an analog thereof represented by structural formula [I] [wherein X- stands for a conjugated base of a Bronsted acid HX such as a carboxylate ion represented by R1COO-, a sulfonate ion represented by R2-SO3
-, a sulfate ion represented by SO4
2- or R3-OSO3
-, a phosphate ion represented by PO4
3-, R4(P=O)(O2
2-) or (R4)2(P=O)(O-), a halogen ion or a conjugated base of a Bronsted acid composed of a Lewis acid ion and a hydrogen halide]. Compared with synthetic methods having been reported in documents, the aforesaid method enables the production of neoponkoranol or an analog thereof (I) in a small number of steps at a high yield.
Inventors:
MURAOKA OSAMU (JP)
TANABE GENZOH (JP)
TANABE GENZOH (JP)
Application Number:
PCT/JP2011/051827
Publication Date:
August 04, 2011
Filing Date:
January 28, 2011
Export Citation:
Assignee:
TAKANO CO LTD (JP)
UNIV KINKI (JP)
MURAOKA OSAMU (JP)
TANABE GENZOH (JP)
UNIV KINKI (JP)
MURAOKA OSAMU (JP)
TANABE GENZOH (JP)
International Classes:
C07D333/46; C07H5/10; C07H15/203
Foreign References:
| JP2009092597A | 2009-04-30 | |||
| JP2005002051A | 2005-01-06 | |||
| JPH08245675A | 1996-09-24 | |||
| JPH08245677A | 1996-09-24 |
Other References:
BLAIR D. JOHNSTON ET AL.: "Synthesis of Sulfonium Sulfate Analogues of Disaccharides and Their Conversion to Chain-Extended Homologues of Salacinol: New Glycosidase Inhibitors", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 3, 2006, pages 1111 - 1118
MICHAUD, T. ET AL.: "Synthesis of monosaccharide-fused azetidines", CARBOHYDRATE RESEARCH, vol. 299, no. 4, 1997, pages 253 - 269
RYE, C.S. ET AL.: "Elucidation of the Mechanism of Polysaccharide Cleavage by Chondroitin AC Lyase from Flavobacterium heparinum", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 33, 2002, pages 9756 - 9767
FUERSTNER, A. ET AL.: "Ring-Closing Alkyne Metathesis. Application to the Total Synthesis of Sophorolipid Lactone", JOURNAL OF ORGANIC CHEMISTRY, vol. 65, no. 25, 2000, pages 8758 - 8762
YOSHIKAWA, M. ET AL.: "Salaprinol and ponkoranol with thio-sugar sulfonium sulfate structure from Slacia prinoides and a-glucosidase inhibitory activity of ponkoranol and kotalanol desulfate", HETEROCYCLES, vol. 75, no. 6, 2008, pages 1397 - 1405
TANABE, G. ET AL.: "Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chainon the a-glucosidase inhibitory activity", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 15, no. 11, 2007, pages 3926 - 3937
CHUNG, S. ET AL.: "Synthesis and biological activities of(4,6-di-O-phosphonato-ยง -D-mannopyranosyl)- methylphosphonate as an analog of 1L-myo-inositol 1,4,5-trisphosphate", CARBOHYDRATE RESEARCH, vol. 260, no. 1, 1994, pages 39 - 50
BERKOWITZ, D.B. ET AL.: "a-Fluorinated Phosphonates as Substrate Mimics for Glucose 6-Phosphate Dehydrogenase: the CHF Stereochemistry Matters", JOURNAL OF ORGANIC CHEMISTRY, vol. 65, no. 15, 2000, pages 4498 - 4508
ESKANDARI, R. ET AL.: "Potent Glucosidase Inhibitors: De-O-sulfonated Ponkoranol and Its Stereoisomer", ORGANIC LETTERS, vol. 12, no. 7, 2010, pages 1632 - 1635
ESKANDARI, R. ET AL.: "Probing the active-site requirements of human intestinal N-terminal maltase glucoamylase: The effect of replacing the sulfate moiety by a methyl ether in ponkoranol, a naturally occurring a-glucosidase inhibitor", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 20, no. 19, 2010, pages 5686 - 5689
MICHAUD, T. ET AL.: "Synthesis of monosaccharide-fused azetidines", CARBOHYDRATE RESEARCH, vol. 299, no. 4, 1997, pages 253 - 269
RYE, C.S. ET AL.: "Elucidation of the Mechanism of Polysaccharide Cleavage by Chondroitin AC Lyase from Flavobacterium heparinum", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 33, 2002, pages 9756 - 9767
FUERSTNER, A. ET AL.: "Ring-Closing Alkyne Metathesis. Application to the Total Synthesis of Sophorolipid Lactone", JOURNAL OF ORGANIC CHEMISTRY, vol. 65, no. 25, 2000, pages 8758 - 8762
YOSHIKAWA, M. ET AL.: "Salaprinol and ponkoranol with thio-sugar sulfonium sulfate structure from Slacia prinoides and a-glucosidase inhibitory activity of ponkoranol and kotalanol desulfate", HETEROCYCLES, vol. 75, no. 6, 2008, pages 1397 - 1405
TANABE, G. ET AL.: "Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chainon the a-glucosidase inhibitory activity", BIOORGANIC & MEDICINAL CHEMISTRY, vol. 15, no. 11, 2007, pages 3926 - 3937
CHUNG, S. ET AL.: "Synthesis and biological activities of(4,6-di-O-phosphonato-ยง -D-mannopyranosyl)- methylphosphonate as an analog of 1L-myo-inositol 1,4,5-trisphosphate", CARBOHYDRATE RESEARCH, vol. 260, no. 1, 1994, pages 39 - 50
BERKOWITZ, D.B. ET AL.: "a-Fluorinated Phosphonates as Substrate Mimics for Glucose 6-Phosphate Dehydrogenase: the CHF Stereochemistry Matters", JOURNAL OF ORGANIC CHEMISTRY, vol. 65, no. 15, 2000, pages 4498 - 4508
ESKANDARI, R. ET AL.: "Potent Glucosidase Inhibitors: De-O-sulfonated Ponkoranol and Its Stereoisomer", ORGANIC LETTERS, vol. 12, no. 7, 2010, pages 1632 - 1635
ESKANDARI, R. ET AL.: "Probing the active-site requirements of human intestinal N-terminal maltase glucoamylase: The effect of replacing the sulfate moiety by a methyl ether in ponkoranol, a naturally occurring a-glucosidase inhibitor", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 20, no. 19, 2010, pages 5686 - 5689
Attorney, Agent or Firm:
MATSUO KENICHIRO (JP)
Ken-ichiro Matsuo (JP)
Ken-ichiro Matsuo (JP)
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