Title:
PREPARATION METHOD FOR ALPHA-PENTA-O-ACETYL MANNOSE
Document Type and Number:
WIPO Patent Application WO/2021/056382
Kind Code:
A1
Abstract:
Provided is a preparation method for alpha-penta-O-acetyl mannose. A study is performed using natural mannose as a raw material on the basis of the conventional acetic anhydride acetylation process. A catalytic amount of cesium fluoride is added as a catalyst. The production of beta-penta-O-acetyl mannose is inhibited under the action of the catalyst, such that a high-purity, solid alpha-penta-O-acetyl mannose can be obtained by direct crystallization and separation, overcoming the obstacles in which crystallizing, purifying and large-scale industrialization of penta-O-acetyl mannose prepared using the conventional method is difficult. The method is simple in process, low in cost, suitable for large-scale production, and can promote the application of mannose in the field of drug and vaccine development.
Inventors:
LI WENJU (CN)
GAO JIAN (CN)
TANG PENGFEI (CN)
ZHUANG YONGZHONG (CN)
LI XIUZHEN (CN)
GAO JIAN (CN)
TANG PENGFEI (CN)
ZHUANG YONGZHONG (CN)
LI XIUZHEN (CN)
Application Number:
PCT/CN2019/108395
Publication Date:
April 01, 2021
Filing Date:
September 27, 2019
Export Citation:
Assignee:
JINAN SAMUEL PHARMACEUTICAL CO LTD (CN)
International Classes:
C07H13/06; C07H1/00; C07H13/08
Domestic Patent References:
| WO2014152718A1 | 2014-09-25 |
Other References:
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AHMADIPOUR, SANAZ ET AL.: "Chemoenzymatic Synthesis of C6-Modified Sugar Nucleotides To Probe the GDP-D-Mannose Dehydrogenase from Pseudomonas aeruginosa", ORG. LETT., vol. 21, 30 May 2019 (2019-05-30), XP055795463
WATT, JACINTA A. ET AL.: "Rapid, iterative assembly of octyl a-1, 6-oligomannosides and their 6-deoxy equivalents", ORG.BIOMOL.CHEM., vol. 3, 20 April 2005 (2005-04-20), XP055795465
ZHANG JIANBO, ZHANG BO, ZHOU JIAFEN, LI JUAN, SHI CHUNJUAN, HUANG TING, WANG ZHONGFU, TANG JIE: "H 2 SO 4 -SiO 2 : Highly Efficient and Reusable Catalyst for per- O -Acetylation of Carbohydrates Under Solvent-Free Conditions", JOURNAL OF CARBOHYDRATE CHEMISTRY, TAYLOR & FRANCIS, UK, vol. 30, no. 3, 1 April 2011 (2011-04-01), UK, pages 165 - 177, XP055795482, ISSN: 0732-8303, DOI: 10.1080/07328303.2011.621042
ROY BIMALENDU, DASGUPTA SOMNATH, KUMAR RAJPUT VISHAL, MUKHOPADHYAY BALARAM: "Samarium Trifluoromethanesulfonate: An Efficient Moisture Tolerant Acylation Catalyst under Solvent‐Free Condition", JOURNAL OF CARBOHYDRATE CHEMISTRY, TAYLOR & FRANCIS, UK, vol. 27, no. 1, 1 May 2008 (2008-05-01), UK, pages 1 - 9, XP055795486, ISSN: 0732-8303, DOI: 10.1080/07328300801991245
CARDOZO HERBERT M., RIBEIRO THAÍS F., SÁ MARCUS M., SEBRÃO DAMIANNI, NASCIMENTO MARIA G., SILVEIRA GUSTAVO P.: "Molecular Sieves Mediated Green Per- O -Acetylation of Carbohydrate Templates and Lipase Catalyzed Regioselective Alcoholysis of 2,3,5-Tri- O -Acetyl-D-Ribonolactone", JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, SOCIEDADE BRASILEIRA DE QUÍMICA, SÃO PAULO; BR, vol. 26, no. 4, 1 January 2015 (2015-01-01), São Paulo; BR, pages 755 - 764, XP055795488, ISSN: 0103-5053, DOI: 10.5935/0103-5053.20150037
AHMADIPOUR, SANAZ ET AL.: "Chemoenzymatic Synthesis of C6-Modified Sugar Nucleotides To Probe the GDP-D-Mannose Dehydrogenase from Pseudomonas aeruginosa", ORG. LETT., vol. 21, 30 May 2019 (2019-05-30), XP055795463
WATT, JACINTA A. ET AL.: "Rapid, iterative assembly of octyl a-1, 6-oligomannosides and their 6-deoxy equivalents", ORG.BIOMOL.CHEM., vol. 3, 20 April 2005 (2005-04-20), XP055795465
ZHANG JIANBO, ZHANG BO, ZHOU JIAFEN, LI JUAN, SHI CHUNJUAN, HUANG TING, WANG ZHONGFU, TANG JIE: "H 2 SO 4 -SiO 2 : Highly Efficient and Reusable Catalyst for per- O -Acetylation of Carbohydrates Under Solvent-Free Conditions", JOURNAL OF CARBOHYDRATE CHEMISTRY, TAYLOR & FRANCIS, UK, vol. 30, no. 3, 1 April 2011 (2011-04-01), UK, pages 165 - 177, XP055795482, ISSN: 0732-8303, DOI: 10.1080/07328303.2011.621042
ROY BIMALENDU, DASGUPTA SOMNATH, KUMAR RAJPUT VISHAL, MUKHOPADHYAY BALARAM: "Samarium Trifluoromethanesulfonate: An Efficient Moisture Tolerant Acylation Catalyst under Solvent‐Free Condition", JOURNAL OF CARBOHYDRATE CHEMISTRY, TAYLOR & FRANCIS, UK, vol. 27, no. 1, 1 May 2008 (2008-05-01), UK, pages 1 - 9, XP055795486, ISSN: 0732-8303, DOI: 10.1080/07328300801991245
CARDOZO HERBERT M., RIBEIRO THAÍS F., SÁ MARCUS M., SEBRÃO DAMIANNI, NASCIMENTO MARIA G., SILVEIRA GUSTAVO P.: "Molecular Sieves Mediated Green Per- O -Acetylation of Carbohydrate Templates and Lipase Catalyzed Regioselective Alcoholysis of 2,3,5-Tri- O -Acetyl-D-Ribonolactone", JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, SOCIEDADE BRASILEIRA DE QUÍMICA, SÃO PAULO; BR, vol. 26, no. 4, 1 January 2015 (2015-01-01), São Paulo; BR, pages 755 - 764, XP055795488, ISSN: 0103-5053, DOI: 10.5935/0103-5053.20150037
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