Title:
METHOD FOR PRODUCING Α-HALO-TETRAACYL GLUCOSE
Document Type and Number:
WIPO Patent Application WO/2014/132940
Kind Code:
A1
Abstract:
Provided is a method for producing α-halo-tetraacyl glucose, the efficiency of which is excellent and suited to industrial production. The present invention is a method for producing α-halo-tetraacyl glucose represented by general formula (III) (R represents an optionally substituted lower alkyl group or an optionally substituted aryl, while X represents a halogen atom) in the first stage thereof from D-glucose or a lower alkyl D-glucoside, by reacting a metal halide and a reactive derivative derived from carboxylic acid. In addition, the present invention pertains to a method for producing a compound or salt thereof represented by formula (I) from the obtained α-halo-tetraacyl glucose (III) by using a known method.
More Like This:
Inventors:
UEDA KEITA (JP)
HATSUDA MASANORI (JP)
HYODO ISAO (JP)
TANIMOTO KOUICHI (JP)
HATSUDA MASANORI (JP)
HYODO ISAO (JP)
TANIMOTO KOUICHI (JP)
Application Number:
PCT/JP2014/054416
Publication Date:
September 04, 2014
Filing Date:
February 25, 2014
Export Citation:
Assignee:
MITSUBISHI TANABE PHARMA CORP (JP)
International Classes:
C07H13/02; C07D409/10; A61K31/381; A61P3/10; C07B61/00; C07H5/02
Domestic Patent References:
| WO2011047113A1 | 2011-04-21 | |||
| WO2012140120A1 | 2012-10-18 | |||
| WO2005012326A1 | 2005-02-10 | |||
| WO2011047113A1 | 2011-04-21 | |||
| WO2012140120A1 | 2012-10-18 |
Foreign References:
| JP2007518683A | 2007-07-12 |
Other References:
GIRI SANTOSH KUMAR ET AL.: "Indium(III) Triflate -Mediated One-Step Preparation of Glycosyl Halides from Free Sugars", SYNTHETIC COMMUNICATIONS, vol. 40, no. 22, 2010, pages 3378 - 3383, XP055285548, DOI: 10.1080/00397910903419886
LEMAIRE SEBASTIEN ET AL.: "Stereoselective C- Glycosylation Reactions with Arylzinc Reagents", ORGANIC LETTERS, vol. 14, no. 6, 1 January 2012 (2012-01-01), pages 1480 - 1483, XP055069093, DOI: 10.1021/OL300220P
PALLAVI TIWARI ET AL.: "ACYLATION OF CARBOHYDRATES OVER A12O3: PREPARATION OF PARTIALLY AND FULLY ACYLATED CARBOHYDRATE DERIVATIVES AND ACETYLATED GLYCOSYL CHLORIDES", CARBOHYDRATE RESEARCH, vol. 341, no. 3, 27 February 2006 (2006-02-27), pages 339 - 350, XP025010362, DOI: 10.1016/J.CARRES.2005.11.035
MO HUNSEN ET AL.: "Mild one-pot preparation of glycosyl bromides", CARBOHYDRATE RESEARCH, vol. 340, no. 17, 12 December 2005 (2005-12-12), pages 2670 - 2674, XP055285561, DOI: 10.1016/J.CARRES.2005.09.016
WENG SHIUE-SHIEN ET AL.: "Facile preparation of a-glycosyl iodides by in situ generated aluminum iodide: straightforward synthesis of thio-, seleno-, and O-glycosides from unprotected reducing sugars", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 29, no. 8-9, 1 January 2011 (2011-01-01), pages 429 - 440, XP055285562, DOI: 10.1080/07328303.2011.565894
HIGASHI KUNIO ET AL.: "Direct transformation of O-glycoside into glycosyl bromide with the combination of trimethylsilyl bromide and zinc bromide", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 39, no. 10, 1 January 1991 (1991-01-01), pages 2502 - 2504, XP055285566, DOI: 10.1248/CPB.39.2502
MURAKAMI TEIICHI ET AL.: "Efficient synthesis of omega-mercaptoalkyl 1,2-trans-glycosides from sugar peracetates", CARBOHYDRATE RESEARCH, vol. 342, no. 8, 11 June 2007 (2007-06-11), pages 1009 - 1020, XP022026765, DOI: 10.1016/J.CARRES.2007.02.024
MURAKAMI TEIICHI ET AL.: "Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters", CARBOHYDRATE RESEARCH, vol. 343, no. 8, 9 June 2008 (2008-06-09), pages 1297 - 1308, XP022648101, DOI: 10.1016/J.CARRES.2008.03.019
WANG QINGBING ET AL.: "A facile preparation of peracylated alpha-aldopyranosyl chlorides with thionyl chloride and tin tetrachloride", CARBOHYDRATE RESEARCH, vol. 343, no. 17, 24 November 2008 (2008-11-24), pages 2989 - 2991, XP025561370, DOI: 10.1016/J.CARRES.2008.08.037
KNOCHEL, P. ET AL.: "Stereoselective C-Glycosylation Reactions with Arylzinc Reagents", ORGANIC LETTERS, vol. 14, no. 6, 2012, pages 1480 - 1483
TIWARI, P. ET AL.: "Acylation of carbohydrates over A1 0 : preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides", CARBOHYDRATE RESEARCH, vol. 341, 2006, pages 339 - 350
GRYNKIEWICZ, G. ET AL.: "Direct transformation of methyl glycopyranosides into corresponding Glycosyl Halides", POLISH J. CHEM., vol. 61, 1987, pages 149 - 153
POLAT, T. ET AL.: "Zinc triflate-benzoyl bromide: a versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides", CARBOHYDRATE RESEARCH, vol. 338, 2003, pages 447 - 449
SANTOSH, K. G.: "Indium(III) tritlate-mediated one-step preparation of Glycosyl halides from free sugars", SYNTHETIC COMMUNICATIONS, vol. 40, 2010, pages 3378 - 3383
ORGANIC LETTERS, vol. 14, no. 6, 2012, pages 1480 - 1483
LEMAIRE SEBASTIEN ET AL.: "Stereoselective C- Glycosylation Reactions with Arylzinc Reagents", ORGANIC LETTERS, vol. 14, no. 6, 1 January 2012 (2012-01-01), pages 1480 - 1483, XP055069093, DOI: 10.1021/OL300220P
PALLAVI TIWARI ET AL.: "ACYLATION OF CARBOHYDRATES OVER A12O3: PREPARATION OF PARTIALLY AND FULLY ACYLATED CARBOHYDRATE DERIVATIVES AND ACETYLATED GLYCOSYL CHLORIDES", CARBOHYDRATE RESEARCH, vol. 341, no. 3, 27 February 2006 (2006-02-27), pages 339 - 350, XP025010362, DOI: 10.1016/J.CARRES.2005.11.035
MO HUNSEN ET AL.: "Mild one-pot preparation of glycosyl bromides", CARBOHYDRATE RESEARCH, vol. 340, no. 17, 12 December 2005 (2005-12-12), pages 2670 - 2674, XP055285561, DOI: 10.1016/J.CARRES.2005.09.016
WENG SHIUE-SHIEN ET AL.: "Facile preparation of a-glycosyl iodides by in situ generated aluminum iodide: straightforward synthesis of thio-, seleno-, and O-glycosides from unprotected reducing sugars", JOURNAL OF CARBOHYDRATE CHEMISTRY, vol. 29, no. 8-9, 1 January 2011 (2011-01-01), pages 429 - 440, XP055285562, DOI: 10.1080/07328303.2011.565894
HIGASHI KUNIO ET AL.: "Direct transformation of O-glycoside into glycosyl bromide with the combination of trimethylsilyl bromide and zinc bromide", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 39, no. 10, 1 January 1991 (1991-01-01), pages 2502 - 2504, XP055285566, DOI: 10.1248/CPB.39.2502
MURAKAMI TEIICHI ET AL.: "Efficient synthesis of omega-mercaptoalkyl 1,2-trans-glycosides from sugar peracetates", CARBOHYDRATE RESEARCH, vol. 342, no. 8, 11 June 2007 (2007-06-11), pages 1009 - 1020, XP022026765, DOI: 10.1016/J.CARRES.2007.02.024
MURAKAMI TEIICHI ET AL.: "Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters", CARBOHYDRATE RESEARCH, vol. 343, no. 8, 9 June 2008 (2008-06-09), pages 1297 - 1308, XP022648101, DOI: 10.1016/J.CARRES.2008.03.019
WANG QINGBING ET AL.: "A facile preparation of peracylated alpha-aldopyranosyl chlorides with thionyl chloride and tin tetrachloride", CARBOHYDRATE RESEARCH, vol. 343, no. 17, 24 November 2008 (2008-11-24), pages 2989 - 2991, XP025561370, DOI: 10.1016/J.CARRES.2008.08.037
KNOCHEL, P. ET AL.: "Stereoselective C-Glycosylation Reactions with Arylzinc Reagents", ORGANIC LETTERS, vol. 14, no. 6, 2012, pages 1480 - 1483
TIWARI, P. ET AL.: "Acylation of carbohydrates over A1 0 : preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides", CARBOHYDRATE RESEARCH, vol. 341, 2006, pages 339 - 350
GRYNKIEWICZ, G. ET AL.: "Direct transformation of methyl glycopyranosides into corresponding Glycosyl Halides", POLISH J. CHEM., vol. 61, 1987, pages 149 - 153
POLAT, T. ET AL.: "Zinc triflate-benzoyl bromide: a versatile reagent for the conversion of ether into benzoate protecting groups and ether glycosides into glycosyl bromides", CARBOHYDRATE RESEARCH, vol. 338, 2003, pages 447 - 449
SANTOSH, K. G.: "Indium(III) tritlate-mediated one-step preparation of Glycosyl halides from free sugars", SYNTHETIC COMMUNICATIONS, vol. 40, 2010, pages 3378 - 3383
ORGANIC LETTERS, vol. 14, no. 6, 2012, pages 1480 - 1483
Attorney, Agent or Firm:
TSUKUNI & ASSOCIATES et al. (JP)
Patent business corporation Tsukuni (JP)
Patent business corporation Tsukuni (JP)
Download PDF:
Previous Patent: SEMICONDUCTOR DEVICE
Next Patent: RESIN COMPOSITION HAVING EXCELLENT SURFACE SMOOTHNESS
Next Patent: RESIN COMPOSITION HAVING EXCELLENT SURFACE SMOOTHNESS