Title:
Manufacturing method of sugar derivative and new sugar derivative
Document Type and Number:
Japanese Patent JP6342968
Kind Code:
B2
Abstract:
PROBLEM TO BE SOLVED: To provide novel sugar derivative production methods which can prepare novel sugar derivatives simply and securely, and to provide novel sugar derivatives which can be produced by the production methods.SOLUTION: The present invention provides a sugar derivative production method which synthesizes a sugar imidazoline derivative or a sugar imidazole derivative by reacting pyranoside oxazoline derivative with a primary amine represented by RaNH[where, Ra is a monovalent organic group without a carbonyl group at a binding terminal], and a novel sugar derivative which can be produced by the production method.SELECTED DRAWING: None
Inventors:
Takashi Kinoshita
Minoru Suda
Wataru Sumiyoshi
Ayaka Ohara
Shoko Ohno
Minoru Suda
Wataru Sumiyoshi
Ayaka Ohara
Shoko Ohno
Application Number:
JP2016216014A
Publication Date:
June 13, 2018
Filing Date:
November 04, 2016
Export Citation:
Assignee:
Fushimi Pharmaceutical Co., Ltd.
International Classes:
C07D233/32; C07D233/64; C07H9/06; C08B37/00
Domestic Patent References:
| JP7059587A | ||||
| JP2008173033A | ||||
| JP11246588A |
Foreign References:
| WO2008111526A1 | ||||
| WO2005010053A1 |
Other References:
HIRANO, S. et al.,Formation of a common imidazole derivative from several 2-acetamido-2-deoxy-N-p-tolyl-β-D-glycosylamines under acetolyzing conditions,Carbohydrate Research,1977年,59(1),pp. 244-247
HIRANO, S. et al.,A novel imidazole derivative from 2-acetamido-2-deoxy-N-p-tolyl-β-D-glucopyranosylamine,Carbohydrate Research,1975年,43(2),pp. 377-379
MAZA, S. et al.,Synthesis of the First Selenium-Containing Acyclic Nucleosides and Anomeric Spironucleosides from Carbohydrate Precursors,European Journal of Organic Chemistry,2009年,(30),pp. 5239-5246
STREITH, J. et al.,The Synthesis of Imidazole Sugars Which Mimic Cyclic Carboxonium Ions Formed During the Glycosidase-Catalyzed Hydrolysis of Oligo- and Polysaccharides,European Journal of Organic Chemistry,1999年,(4),pp. 893-898
DEREDAS, D. et al.,Synthesis of D-erythrofuranosyl C-nucleosides of imidazole from 4(5)-(D-arabino-tetritol-1-yl)imidazole,Carbohydrate Research,1994年,252,pp. 275-281
FERNANDEZ-BOLANOS, J. et al.,Imidazole surfactants. II. Synthesis of 1-alkyl-4-D-lyxo-tetrahydroxybutyl-1H-imidazoles,Grasas y Aceites,1990年,41(1),pp. 1-5
RUIZ Contreras, R. et al.,Imidazole surfactants. IV. Synthesis of 3-(1-alkyl-1H-imidazol-4-yl)-2-propenoic acids,Grasas y Aceites,1990年,41(4-5),pp. 332-335
FERNANDEZ-BOLANOS, J. et al.,Glucimidazoles. V. 1-n-Alkyl-4-D-arabino-tetrahydroxybutyl-1H-imidazoles,Anales de Quimica, Serie C: Quimica Organica y Bioquimica,1984年,80(2),pp. 195-197
FERNANDEZ-BOLANOS, J. et al.,Glycoimidazoles. I. 4-D-Arabino-tetrahydroxybutylimidazoles,Anales de Quimica,1968年,64(2),pp. 203-208
HUBER, G. et al.,Imidazole derivatives from 1-amino-1-deoxy-D-fructose,Helvetica Chimica Acta,1960年,43,pp. 1787-1795
UMEKAWA, M. et al.,Efficient transfer of sialo-oligosaccharide onto proteins by combined use of a glycosynthase-like mutant of Mucor hiemalis endoglycosidase and synthetic sialo-complex-type sugar oxazoline,Biochimica et Biophysica Acta,2010年,1800(11),pp. 1203-1209
NOGUCHI, M. et al.,A Practical One-Step Synthesis of 1,2-Oxazoline Derivatives from Unprotected Sugars and Its Application to Chemoenzymatic β-N-Acetylglucosaminidation of Disialo-oligosaccharide,Helvetica Chimica Acta,2012年,95(10),pp. 1928-1936
HIRANO, S. et al.,A novel imidazole derivative from 2-acetamido-2-deoxy-N-p-tolyl-β-D-glucopyranosylamine,Carbohydrate Research,1975年,43(2),pp. 377-379
MAZA, S. et al.,Synthesis of the First Selenium-Containing Acyclic Nucleosides and Anomeric Spironucleosides from Carbohydrate Precursors,European Journal of Organic Chemistry,2009年,(30),pp. 5239-5246
STREITH, J. et al.,The Synthesis of Imidazole Sugars Which Mimic Cyclic Carboxonium Ions Formed During the Glycosidase-Catalyzed Hydrolysis of Oligo- and Polysaccharides,European Journal of Organic Chemistry,1999年,(4),pp. 893-898
DEREDAS, D. et al.,Synthesis of D-erythrofuranosyl C-nucleosides of imidazole from 4(5)-(D-arabino-tetritol-1-yl)imidazole,Carbohydrate Research,1994年,252,pp. 275-281
FERNANDEZ-BOLANOS, J. et al.,Imidazole surfactants. II. Synthesis of 1-alkyl-4-D-lyxo-tetrahydroxybutyl-1H-imidazoles,Grasas y Aceites,1990年,41(1),pp. 1-5
RUIZ Contreras, R. et al.,Imidazole surfactants. IV. Synthesis of 3-(1-alkyl-1H-imidazol-4-yl)-2-propenoic acids,Grasas y Aceites,1990年,41(4-5),pp. 332-335
FERNANDEZ-BOLANOS, J. et al.,Glucimidazoles. V. 1-n-Alkyl-4-D-arabino-tetrahydroxybutyl-1H-imidazoles,Anales de Quimica, Serie C: Quimica Organica y Bioquimica,1984年,80(2),pp. 195-197
FERNANDEZ-BOLANOS, J. et al.,Glycoimidazoles. I. 4-D-Arabino-tetrahydroxybutylimidazoles,Anales de Quimica,1968年,64(2),pp. 203-208
HUBER, G. et al.,Imidazole derivatives from 1-amino-1-deoxy-D-fructose,Helvetica Chimica Acta,1960年,43,pp. 1787-1795
UMEKAWA, M. et al.,Efficient transfer of sialo-oligosaccharide onto proteins by combined use of a glycosynthase-like mutant of Mucor hiemalis endoglycosidase and synthetic sialo-complex-type sugar oxazoline,Biochimica et Biophysica Acta,2010年,1800(11),pp. 1203-1209
NOGUCHI, M. et al.,A Practical One-Step Synthesis of 1,2-Oxazoline Derivatives from Unprotected Sugars and Its Application to Chemoenzymatic β-N-Acetylglucosaminidation of Disialo-oligosaccharide,Helvetica Chimica Acta,2012年,95(10),pp. 1928-1936
Attorney, Agent or Firm:
Naomi Kamino
Tetsuji Kamidai
Tetsuji Kamidai