Title:
METHOD FOR PRODUCING ACYL GLUCURONIDE
Document Type and Number:
WIPO Patent Application WO/2013/157267
Kind Code:
A1
Abstract:
[Problem] To provide a novel method for producing an acyl glucuronide which is an ester compound of a compound containing a carboxy group and a glucuronic acid. [Solution] An acyl glucuronide is obtained, for example, by reacting 1-chloro-N,N,2-trimethyl propenylamine (tetramethyl chloroenamine, TMCE) with a carboxylic acid, then reacting the obtained compound with 2,3,4-tri-O-allyloxycarbonyl-D-glucuronic acid allyl, and performing a deprotection treatment. In addition, 2,3,4-tri-O-allyloxycarbonyl-D-glucuronic acid allyl can be produced inexpensively and safely by reacting 1,2,3,4-tetra-O-allyloxycarbonyl-D-glucuronic acid allyl with an amine such as ammonia or pyrrolidine.
Inventors:
NAGAO MUNEKI (JP)
SUZUKI MASASHI (JP)
SUZUKI MASASHI (JP)
Application Number:
PCT/JP2013/002618
Publication Date:
October 24, 2013
Filing Date:
April 18, 2013
Export Citation:
Assignee:
KYORIN SEIYAKU KK (JP)
International Classes:
C07H13/04; C07H13/08; C07H13/10
Other References:
ALAIN DE MESMAEKER ET AL.: "A new protected form of glucuronic acid for the synthesis of labile 1-O-acyl-beta-D-glucuronides", TETRAHEDRON LETT., vol. 30, no. 29, 1989, pages 3773 - 3776
ABDESSAMED EL ALAOUI ET AL.: "Protecting groups for glucuronic acid- Application to the synyhesis of new paclitaxel (Taxol) derivatives", J. ORG. CHEM., vol. 71, 2006, pages 9628 - 9636
ANDERS BERGH ET AL.: "Carbohydrate functionalization using cationic iron carbonyl complexes", CARBOHYDR. RES., vol. 343, 2008, pages 1808 - 1813
JOSE FIANDOR ET AL.: "Hexose-modified anti-viral analogues of uridine 5'-diphosphate glucose derivatives", EUR. J. MED. CHEM., vol. 22, 1987, pages 59 - 65
HERRY GUNADI SUDIBYA ET AL.: "Interfacing glycosylated carbon-nanotube-network devices with living cells to detect dynamic secretion of biomolecules", ANGEW. CHEM. INT. ED., vol. 48, no. 15, 2009, pages 2723 - 2726
DALE L. BOGER ET AL.: "Key synthetic analogs of Bleomycin A2 that directly address the effect and role of the disaccharide - Demannosylbleomycin A2 and alpha-D- Mannopyranosyldeglycobleomycin A2", J. AM. CHEM. SOC., vol. 117, no. 28, 1995, pages 7344 - 7356
MUI MUI SIM ET AL.: "Synthesis and use of Glycosyl Phosphites -An effective route to Glycosyl Phosphates, Sugar Nucleotides and Glycosides", J. AM. CHEM. SOC., vol. 115, no. 6, 1993, pages 2260 - 2267
ABDESSAMED EL ALAOUI ET AL.: "Protecting groups for glucuronic acid- Application to the synyhesis of new paclitaxel (Taxol) derivatives", J. ORG. CHEM., vol. 71, 2006, pages 9628 - 9636
ANDERS BERGH ET AL.: "Carbohydrate functionalization using cationic iron carbonyl complexes", CARBOHYDR. RES., vol. 343, 2008, pages 1808 - 1813
JOSE FIANDOR ET AL.: "Hexose-modified anti-viral analogues of uridine 5'-diphosphate glucose derivatives", EUR. J. MED. CHEM., vol. 22, 1987, pages 59 - 65
HERRY GUNADI SUDIBYA ET AL.: "Interfacing glycosylated carbon-nanotube-network devices with living cells to detect dynamic secretion of biomolecules", ANGEW. CHEM. INT. ED., vol. 48, no. 15, 2009, pages 2723 - 2726
DALE L. BOGER ET AL.: "Key synthetic analogs of Bleomycin A2 that directly address the effect and role of the disaccharide - Demannosylbleomycin A2 and alpha-D- Mannopyranosyldeglycobleomycin A2", J. AM. CHEM. SOC., vol. 117, no. 28, 1995, pages 7344 - 7356
MUI MUI SIM ET AL.: "Synthesis and use of Glycosyl Phosphites -An effective route to Glycosyl Phosphates, Sugar Nucleotides and Glycosides", J. AM. CHEM. SOC., vol. 115, no. 6, 1993, pages 2260 - 2267
Attorney, Agent or Firm:
MIZUNO, Katsufumi et al. (JP)
Katsufumi Mizuno (JP)
Katsufumi Mizuno (JP)
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