Title:
ZOLINOSE COMPOUND, PREPARATION METHOD THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/078487
Kind Code:
A1
Abstract:
The present disclosure provides a zolinose compound represented by formula (I), a preparation method therefor and a use thereof, wherein definitions of substituents are provided in the description. The zolinose compound has application prospect in asymmetric synthesis of complex molecules, site-selective modification of sugar rings, flexible assembly of oligosaccharides and glycopeptides, and specific glycosylation modification of peptides and proteins, and provides a novel zolinose-based synthesis toolkit for medical chemistry or chemical biology research.
Inventors:
ZHU WEILIANG (CN)
LI BO (CN)
DONG SANFENG (CN)
ZHAO YITIAN (CN)
JIA QI (CN)
ZHANG YONG (CN)
XU ZHIJIAN (CN)
CHEN KAIXIAN (CN)
LI BO (CN)
DONG SANFENG (CN)
ZHAO YITIAN (CN)
JIA QI (CN)
ZHANG YONG (CN)
XU ZHIJIAN (CN)
CHEN KAIXIAN (CN)
Application Number:
PCT/CN2021/124009
Publication Date:
April 21, 2022
Filing Date:
October 15, 2021
Export Citation:
Assignee:
SHANGHAI INST MATERIA MEDICA CAS (CN)
International Classes:
C07D309/32; C07H13/04; C07D498/04; C07D498/14; C07H1/00; C07H9/06; C07H13/08; C07H15/18; C07H15/203; C07K7/06
Other References:
DONG SANFENG, ZHAO YITIAN, SHI YULONG, XU ZHIJIAN, SHEN JINGSHAN, JIA QI, LI YIMING, CHEN KAIXIAN, LI BO, ZHU WEILIANG: "One step stereoselective synthesis of oxazoline-fused saccharides and their conversion into the corresponding 1,2- cis glycosylamines bearing various protected groups", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 19, no. 7, 25 February 2021 (2021-02-25), pages 1580 - 1588, XP055921246, ISSN: 1477-0520, DOI: 10.1039/D0OB02477E
GRATIA SYNTHIA S.; VIGNEAU EDWARD S.; ELTAYEB SUMIEA; PATEL KISHAN; MEYERHOEFER TERENCE J.; KERSHAW SONIA; HUANG VICTOR; DE CASTRO: "A facile preparation of various N-heterocycles using amides and olefins", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 55, no. 2, 8 January 2014 (2014-01-08), Amsterdam , NL , pages 448 - 452, XP028806065, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2013.11.054
BATOUX, N. ; HARDACRE, C. ; MIGAUD, M.E. ; NESS, K.A. ; NORMAN, S.E.: "Reactivity of 1,2-cyclic sulfite xylosides towards nucleophiles", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 65, no. 43, 24 October 2009 (2009-10-24), AMSTERDAM, NL , pages 8858 - 8862, XP026623894, ISSN: 0040-4020, DOI: 10.1016/j.tet.2009.08.053
SILVA, S. ; TARDY, S. ; ROUTIER, S. ; SUZENET, F. ; TATIBOUET, A. ; RAUTER, A.P. ; ROLLIN, P.: "1,3-Oxazoline- and 1,3-oxazolidine-2-thiones as substrates in direct modified Stille and Suzuki cross-coupling", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 49, no. 39, 22 September 2008 (2008-09-22), Amsterdam , NL , pages 5583 - 5586, XP023902272, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2008.07.023
LECONTE NICOLAS, PELLEGATTI LAURENT, TATIBOUËT ARNAUD, SUZENET FRANCK, ROLLIN PATRICK, GUILLAUMET GERALD: "Benzylsulfanyloxazolines in Palladium-Catalyzed Cross-Coupling Reactions: A Novel Approach to Chiral Oxazolines", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 2007, no. 6, 1 March 2007 (2007-03-01), STUTTGART, DE. , pages 857 - 864, XP055921249, ISSN: 0039-7881, DOI: 10.1055/s-2007-965932
FISERA LUBOR, LAUDAR SAMUEL, TIMPE HANS-JOACHIM, ZALUPSKY PETER, STIBRANYI LADISLAV: "Preparation and photochemistry of furoisoxazolines. An extraordinarily unambiguous photo-induced rearrangement", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY, ACADEMY OF SCIENCES OF THE CZECH REPUBLIC, CZ, vol. 49, no. 5, 1 May 1984 (1984-05-01), CZ , pages 1193 - 1203, XP055921250, ISSN: 0010-0765, ISBN: 978-80-86241-25-8, DOI: 10.1135/cccc19841193
QIAN SHAN, CHEN QUAN LONG, GUAN JIN LONG, WU YONG, WANG ZHOU YU: "Synthesis and Biological Evaluation of Raddeanin A, a Triterpene Saponin Isolated from Anemone raddeana", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 62, no. 8, 1 August 2014 (2014-08-01), JP , pages 779 - 785, XP055921253, ISSN: 0009-2363, DOI: 10.1248/cpb.c14-00138
KLEIN HOLGER, MIETCHEN RALF, REINKE HELMUT, MICHALIK MANFRED: "HF-unterstützte Synthese von Orthoestern und Oxazolinen. [1]", JOURNAL FUER PRAKTISCHE CHEMIE., WILEY VCH, WEINHEIM., DE, vol. 341, no. 1, 1 January 1999 (1999-01-01), DE , pages 41 - 46, XP055921255, ISSN: 1436-9966, DOI: 10.1002/(SICI)1521-3897(199901)341:1<41::AID-PRAC41>3.0.CO;2-L
GRATIA SYNTHIA S.; VIGNEAU EDWARD S.; ELTAYEB SUMIEA; PATEL KISHAN; MEYERHOEFER TERENCE J.; KERSHAW SONIA; HUANG VICTOR; DE CASTRO: "A facile preparation of various N-heterocycles using amides and olefins", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 55, no. 2, 8 January 2014 (2014-01-08), Amsterdam , NL , pages 448 - 452, XP028806065, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2013.11.054
BATOUX, N. ; HARDACRE, C. ; MIGAUD, M.E. ; NESS, K.A. ; NORMAN, S.E.: "Reactivity of 1,2-cyclic sulfite xylosides towards nucleophiles", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 65, no. 43, 24 October 2009 (2009-10-24), AMSTERDAM, NL , pages 8858 - 8862, XP026623894, ISSN: 0040-4020, DOI: 10.1016/j.tet.2009.08.053
SILVA, S. ; TARDY, S. ; ROUTIER, S. ; SUZENET, F. ; TATIBOUET, A. ; RAUTER, A.P. ; ROLLIN, P.: "1,3-Oxazoline- and 1,3-oxazolidine-2-thiones as substrates in direct modified Stille and Suzuki cross-coupling", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 49, no. 39, 22 September 2008 (2008-09-22), Amsterdam , NL , pages 5583 - 5586, XP023902272, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2008.07.023
LECONTE NICOLAS, PELLEGATTI LAURENT, TATIBOUËT ARNAUD, SUZENET FRANCK, ROLLIN PATRICK, GUILLAUMET GERALD: "Benzylsulfanyloxazolines in Palladium-Catalyzed Cross-Coupling Reactions: A Novel Approach to Chiral Oxazolines", SYNTHESIS, GEORG THIEME VERLAG, STUTTGART, DE., vol. 2007, no. 6, 1 March 2007 (2007-03-01), STUTTGART, DE. , pages 857 - 864, XP055921249, ISSN: 0039-7881, DOI: 10.1055/s-2007-965932
FISERA LUBOR, LAUDAR SAMUEL, TIMPE HANS-JOACHIM, ZALUPSKY PETER, STIBRANYI LADISLAV: "Preparation and photochemistry of furoisoxazolines. An extraordinarily unambiguous photo-induced rearrangement", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY, ACADEMY OF SCIENCES OF THE CZECH REPUBLIC, CZ, vol. 49, no. 5, 1 May 1984 (1984-05-01), CZ , pages 1193 - 1203, XP055921250, ISSN: 0010-0765, ISBN: 978-80-86241-25-8, DOI: 10.1135/cccc19841193
QIAN SHAN, CHEN QUAN LONG, GUAN JIN LONG, WU YONG, WANG ZHOU YU: "Synthesis and Biological Evaluation of Raddeanin A, a Triterpene Saponin Isolated from Anemone raddeana", CHEMICAL AND PHARMACEUTICAL BULLETIN, PHARMACEUTICAL SOCIETY OF JAPAN, JP, vol. 62, no. 8, 1 August 2014 (2014-08-01), JP , pages 779 - 785, XP055921253, ISSN: 0009-2363, DOI: 10.1248/cpb.c14-00138
KLEIN HOLGER, MIETCHEN RALF, REINKE HELMUT, MICHALIK MANFRED: "HF-unterstützte Synthese von Orthoestern und Oxazolinen. [1]", JOURNAL FUER PRAKTISCHE CHEMIE., WILEY VCH, WEINHEIM., DE, vol. 341, no. 1, 1 January 1999 (1999-01-01), DE , pages 41 - 46, XP055921255, ISSN: 1436-9966, DOI: 10.1002/(SICI)1521-3897(199901)341:1<41::AID-PRAC41>3.0.CO;2-L
Attorney, Agent or Firm:
KINGSOUND & PARTNERS (CN)
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