Title:
OLIGOSACCHARIDE C-GLYCOSIDE DERIVATIVES
Document Type and Number:
WIPO Patent Application WO/2019/182087
Kind Code:
A1
Abstract:
The present invention provides a novel process for preparing an oligosaccharide C-glycoside derivative of formula I, comprising reacting a compound of formula II with compound of formula III in the presence of at least one primary or secondary amine and at least one additive [in the formulae, the substituents are as defined herein], and novel oligosaccharide C-glycoside derivatives that can be prepared using the process.
Inventors:
TANAKA FUJIE (JP)
JOHNSON SHERIDA (JP)
JOHNSON SHERIDA (JP)
Application Number:
PCT/JP2019/011994
Publication Date:
September 26, 2019
Filing Date:
March 22, 2019
Export Citation:
Assignee:
OKINAWA INST SCIENCE & TECH SCHOOL CORP (JP)
International Classes:
C07H17/04
Domestic Patent References:
| WO2002051803A2 | 2002-07-04 | |||
| WO2016151989A1 | 2016-09-29 | |||
| WO2016151989A1 | 2016-09-29 |
Foreign References:
| US8314219B1 | 2012-11-20 | |||
| US20080081905A1 | 2008-04-03 | |||
| US20080153760A1 | 2008-06-26 | |||
| US20110245490A1 | 2011-10-06 | |||
| US20080193400A1 | 2008-08-14 | |||
| US201862647241P | 2018-03-23 |
Other References:
CARPENTER, C. A. ET AL.: "Preparation of saturated and unsaturated fatty acid hydrazides and long chain C-glycoside ketohydrazones", GREEN CHEMISTRY, vol. 12, no. 11, 2010, pages 2012 - 2018, XP55639553
BISHT, S. S. ET AL.: "Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 19, no. 10, 2009, pages 2699 - 2703, XP026085946
RODRIGUES, F. ET AL.: "A convenient, one-step, synthesis of beta-C-glycosidic ketones in aqueous media", CHEMICAL COMMUNICATIONS, 2000, Cambridge, pages 2049 - 2050, XP002174157
XIAOFENG WEI,† SHILIANG SHI,†,‡ XIAOWEI XIE,† YOHEI SHIMIZU,*,† AND MOTOMU KANAI*,† : "Copper(I)-Catalyzed Dehydrative C Glycosidation of Unprotected Pyranoses with Ketones", ACS CATALYSIS, vol. 6, no. 10, 2016, pages 6718 - 6722, XP009522889, ISSN: 2155-5435
RANOUX, A. ET AL.: "Horner-Wadsworth-Emmons Reaction of Unprotected Sugars in Water or in the Absence of Any Solvent: One-Step Access to C -Glycoside Amphiphiles", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, pages 1314 - 1323, XP55639563
CAVEZZA, A. ET AL., BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 19, no. 3, 2009, pages 845 - 849, XP025925835
FENG, W. ET AL.: "Microwave-assisted efficient synthesis of aryl ketone Breta-C-glycosides from unprotected aldoses", CARBOHYDRATE RESEARCH, vol. 346, no. 2, 2011, pages 352 - 356, XP027600744
WEI-WEI FENG, ZHI-JIE FANG, WEI GUO, YAN-FEI XIANG: "Concise synthesis of beta-glucosidase inhibitors alpha-bromoacetone-beta-C-glycosides", HUAXUE SHIJI, vol. 35, no. 6, 2013, pages 561 - 563 , 566, XP009522887, ISSN: 0258-3283
HERSANT, Y. ET AL.: "One-step synthesis of Beta-C-glycolipid derivatives from unprotected sugars", CARBOHYDRATE RESEARCH, vol. 339, no. 3, 2004, pages 741 - 745, XP027114459
HOWARD, S. ET AL.: "Bromoketone C-Glycosides, a New Class of -Glucanase Inactivators", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 120, no. 40, 1998, pages 10326 - 10331, XP55639606
ZHDANOV, Y. A. ET AL.: "INTERACTION OF PARTIALLY SCREENED ALDOSES WITH P- METHOXYBENZOYLMETHYLENEPHOSPHORANE", ZHURNAL OBSHCHEI KHIMII, vol. 39, no. 1, 1969, pages 119 - 122, XP009052287
FENGER, T. H. ET AL.: "Synthesis and Analysis of Specific Covalent Inhibitors of endo -Xyloglucanases", CHEMBIOCHEM, vol. 16, no. 4, 2015, pages 575 - 583, XP55639617
JOHNSON, S. ET AL.: "Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation-oxa-Michael reactions with unactivated ketones", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 14, no. 1, 2016, pages 259 - 264, XP055318293
JOHNSON, S. ET AL.: "Leveraging a “Catch-Release” Logic Gate Process for the Synthesis and Nonchromatographic Purification of Thioether- or Amine-Bridged Macrocyclic Peptides", JOURNAL OF ORGANIC CHEMISTRY, vol. 83, no. 8, 29 March 2018 (2018-03-29), pages 4581 - 4597, XP055555586
JOHNSON SHERIDA ET AL.: "Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation-oxa-Michael reactions with unactivated ketones", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 14, 2016, pages 259 - 264, XP055318293, DOI: 10.1039/C5OB02094H
JOHNSON SHERIDA ET AL.: "C-glycosidation of Unprotected di- and trisaccharides aldopyranoses with Ketones Using Pyrrolidine-Boric Acid Catalysis", JOURNAL OF ORGANIC CHEMISTRY, vol. 83, no. 8, 29 March 2018 (2018-03-29), pages 4584 - 4597
JOHNSON, S.TANAKA, F, ORG. BIOMOL. CHEM., vol. 14, 2016, pages 259 - 264
RICHTER, C.KRUMREY, M.BAHRI, M.TRUNSCHKE, S.MAHRWALD, R., ACS CATAL, vol. 6, 2016, pages 5549 - 5552
BENVEGNU, T., EUR. J. ORG. CHEM., 2010, pages 1314 - 1323
CUI, H.-L.CHOUTHA IWALE, P. V.YIN, F.TANAKA, F, ASIAN J. ORG. CHEM., vol. 5, 2016, pages 153 - 161
See also references of EP 3768693A1
BISHT, S. S. ET AL.: "Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 19, no. 10, 2009, pages 2699 - 2703, XP026085946
RODRIGUES, F. ET AL.: "A convenient, one-step, synthesis of beta-C-glycosidic ketones in aqueous media", CHEMICAL COMMUNICATIONS, 2000, Cambridge, pages 2049 - 2050, XP002174157
XIAOFENG WEI,† SHILIANG SHI,†,‡ XIAOWEI XIE,† YOHEI SHIMIZU,*,† AND MOTOMU KANAI*,† : "Copper(I)-Catalyzed Dehydrative C Glycosidation of Unprotected Pyranoses with Ketones", ACS CATALYSIS, vol. 6, no. 10, 2016, pages 6718 - 6722, XP009522889, ISSN: 2155-5435
RANOUX, A. ET AL.: "Horner-Wadsworth-Emmons Reaction of Unprotected Sugars in Water or in the Absence of Any Solvent: One-Step Access to C -Glycoside Amphiphiles", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, pages 1314 - 1323, XP55639563
CAVEZZA, A. ET AL., BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 19, no. 3, 2009, pages 845 - 849, XP025925835
FENG, W. ET AL.: "Microwave-assisted efficient synthesis of aryl ketone Breta-C-glycosides from unprotected aldoses", CARBOHYDRATE RESEARCH, vol. 346, no. 2, 2011, pages 352 - 356, XP027600744
WEI-WEI FENG, ZHI-JIE FANG, WEI GUO, YAN-FEI XIANG: "Concise synthesis of beta-glucosidase inhibitors alpha-bromoacetone-beta-C-glycosides", HUAXUE SHIJI, vol. 35, no. 6, 2013, pages 561 - 563 , 566, XP009522887, ISSN: 0258-3283
HERSANT, Y. ET AL.: "One-step synthesis of Beta-C-glycolipid derivatives from unprotected sugars", CARBOHYDRATE RESEARCH, vol. 339, no. 3, 2004, pages 741 - 745, XP027114459
HOWARD, S. ET AL.: "Bromoketone C-Glycosides, a New Class of -Glucanase Inactivators", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 120, no. 40, 1998, pages 10326 - 10331, XP55639606
ZHDANOV, Y. A. ET AL.: "INTERACTION OF PARTIALLY SCREENED ALDOSES WITH P- METHOXYBENZOYLMETHYLENEPHOSPHORANE", ZHURNAL OBSHCHEI KHIMII, vol. 39, no. 1, 1969, pages 119 - 122, XP009052287
FENGER, T. H. ET AL.: "Synthesis and Analysis of Specific Covalent Inhibitors of endo -Xyloglucanases", CHEMBIOCHEM, vol. 16, no. 4, 2015, pages 575 - 583, XP55639617
JOHNSON, S. ET AL.: "Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation-oxa-Michael reactions with unactivated ketones", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 14, no. 1, 2016, pages 259 - 264, XP055318293
JOHNSON, S. ET AL.: "Leveraging a “Catch-Release” Logic Gate Process for the Synthesis and Nonchromatographic Purification of Thioether- or Amine-Bridged Macrocyclic Peptides", JOURNAL OF ORGANIC CHEMISTRY, vol. 83, no. 8, 29 March 2018 (2018-03-29), pages 4581 - 4597, XP055555586
JOHNSON SHERIDA ET AL.: "Direct synthesis of C-glycosides from unprotected 2-N-acyl-aldohexoses via aldol condensation-oxa-Michael reactions with unactivated ketones", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 14, 2016, pages 259 - 264, XP055318293, DOI: 10.1039/C5OB02094H
JOHNSON SHERIDA ET AL.: "C-glycosidation of Unprotected di- and trisaccharides aldopyranoses with Ketones Using Pyrrolidine-Boric Acid Catalysis", JOURNAL OF ORGANIC CHEMISTRY, vol. 83, no. 8, 29 March 2018 (2018-03-29), pages 4584 - 4597
JOHNSON, S.TANAKA, F, ORG. BIOMOL. CHEM., vol. 14, 2016, pages 259 - 264
RICHTER, C.KRUMREY, M.BAHRI, M.TRUNSCHKE, S.MAHRWALD, R., ACS CATAL, vol. 6, 2016, pages 5549 - 5552
BENVEGNU, T., EUR. J. ORG. CHEM., 2010, pages 1314 - 1323
CUI, H.-L.CHOUTHA IWALE, P. V.YIN, F.TANAKA, F, ASIAN J. ORG. CHEM., vol. 5, 2016, pages 153 - 161
See also references of EP 3768693A1
Attorney, Agent or Firm:
TSUKUNI & ASSOCIATES et al. (JP)
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