Title:
PROCESS FOR PRODUCING GLYCOSIDE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2006/038440
Kind Code:
A1
Abstract:
A novel process for producing a phenylglycoside derivative which comprises using an unprotected sugar as a starting material and causing a compound having a phenolic hydroxy group to act on the sugar. The phenylglycoside derivative is attracting attention as a substrate for enzymatic activity assay, a diagnostic drug, or a useful intermediate for synthesis. There is a strong desire for a process for the production thereof which can be practiced industrially and is inexpensive and easier. The process, in which an unprotected sugar as a starting material is used to obtain the corresponding phenylglycoside derivative therefrom through one stage, comprises using the Mitsunobu reagent to conduct one-stage dehydrating condensation to thereby obtain the phenylglycoside derivative. In the process, there is no need of conducting the protection of hydroxy groups and elimination of the protective groups which have conventionally been necessary.
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Inventors:
SHODA SHINICHIRO (JP)
KOBAYASHI ATSUSHI (JP)
TAKAHASHI SATOSHI (JP)
KOBAYASHI ATSUSHI (JP)
TAKAHASHI SATOSHI (JP)
Application Number:
PCT/JP2005/016850
Publication Date:
April 13, 2006
Filing Date:
September 13, 2005
Export Citation:
Assignee:
UNIV TOHOKU (JP)
SHODA SHINICHIRO (JP)
KOBAYASHI ATSUSHI (JP)
TAKAHASHI SATOSHI (JP)
SHODA SHINICHIRO (JP)
KOBAYASHI ATSUSHI (JP)
TAKAHASHI SATOSHI (JP)
International Classes:
C07H15/203
Other References:
ABBOTT B.J. ET AL: "Glucosylation of Mycophenolic Acid by Streptomyces Aureofaciens", THE JOURNAL OF ANTIBIOTICS, vol. 33, no. 5, May 1980 (1980-05-01), pages 506 - 509, XP002993095
KIESLICH K. ET AL: "Mikrobiologische Umwandlungen nichtsteroider Strukturen, VII, Mikrobielle Glucosiderung einer phenolischen Hydroxylgruppe", CHEMISCHE BERICHTE, vol. 109, no. 6, 1976, pages 2259 - 2265, XP002993096
TOKUTAKE S. ET AL: "Glycosides Having Chromophores as Substrates for Sensitive Enzyme Analysis. I. Synthesis of Phenolindophenyl-beta-D-glucopyranosides as Substrates for beta-Glucosidase", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 38, no. 1, 1990, pages 13 - 18, XP002137365
BADMAN G.T. ET AL: "A novel synthesis of beta-phenylglucuronides using the Mitsunobu reaction; an application of phenolic chromium tricarbonyl complexes", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 388, no. 1-2, 1990, pages 117 - 121, XP002993097
ROUSH W.R. AND LIN X.-F.: "A Highly Stereoselective Synthesis of Aryl 2-Deoxy-beta-glycosides via the Mitsunobu Reaction", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 56, no. 20, 1991, pages 5740 - 5742, XP002993098
CHIBA N. ET AL: "Total Synthesis of Antibiotic Hygromycin A", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 56, no. 9, 1991, pages 2976 - 2983, XP002993099
BOUALI A. ET AL: "Derivatisation of 1,3,4,6-tetra-0-benzoyl-alpha-d-fructofuranose at the anomeric site: O-Alkylation, 0-Acylation, O-Arylation, Amination and Selenation Reactions", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 11, no. 2, 1992, pages 159 - 169, XP002993100
KOMETANI T. ET AL: "Boron Trifluoride Catalyzed Rearrangement of 2-Aryloxytetrahydropyrans: A New Entry to C-Arylglycosidation", SYNTHESIS, no. 12, December 1988 (1988-12-01), pages 1005 - 1007, XP002993601
KIESLICH K. ET AL: "Mikrobiologische Umwandlungen nichtsteroider Strukturen, VII, Mikrobielle Glucosiderung einer phenolischen Hydroxylgruppe", CHEMISCHE BERICHTE, vol. 109, no. 6, 1976, pages 2259 - 2265, XP002993096
TOKUTAKE S. ET AL: "Glycosides Having Chromophores as Substrates for Sensitive Enzyme Analysis. I. Synthesis of Phenolindophenyl-beta-D-glucopyranosides as Substrates for beta-Glucosidase", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 38, no. 1, 1990, pages 13 - 18, XP002137365
BADMAN G.T. ET AL: "A novel synthesis of beta-phenylglucuronides using the Mitsunobu reaction; an application of phenolic chromium tricarbonyl complexes", JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 388, no. 1-2, 1990, pages 117 - 121, XP002993097
ROUSH W.R. AND LIN X.-F.: "A Highly Stereoselective Synthesis of Aryl 2-Deoxy-beta-glycosides via the Mitsunobu Reaction", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 56, no. 20, 1991, pages 5740 - 5742, XP002993098
CHIBA N. ET AL: "Total Synthesis of Antibiotic Hygromycin A", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 56, no. 9, 1991, pages 2976 - 2983, XP002993099
BOUALI A. ET AL: "Derivatisation of 1,3,4,6-tetra-0-benzoyl-alpha-d-fructofuranose at the anomeric site: O-Alkylation, 0-Acylation, O-Arylation, Amination and Selenation Reactions", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 11, no. 2, 1992, pages 159 - 169, XP002993100
KOMETANI T. ET AL: "Boron Trifluoride Catalyzed Rearrangement of 2-Aryloxytetrahydropyrans: A New Entry to C-Arylglycosidation", SYNTHESIS, no. 12, December 1988 (1988-12-01), pages 1005 - 1007, XP002993601
Attorney, Agent or Firm:
Shigenobu, Kazuo (3-28 Kioi-ch, Chiyoda-ku Tokyo 94, JP)
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