Title:
PROGRAMMABLE SELECTIVE ACYLATION OF POLYOLS
Document Type and Number:
WIPO Patent Application WO/2023/059266
Kind Code:
A3
Abstract:
Disclosed herein is a method to selectively acylate a polyol, the method comprising the steps of: (a) providing a mixture comprising a polyol, an acylation agent, a N-heterocyclic carbene (NHC) precursor, a base and a solvent; and (b) subjecting the mixture to an elevated temperature for a period of time to provide a selectively acylated polyol, optionally wherein the mixture further comprises a boronic acid.
Inventors:
CHI YONGGUI (SG)
LYU WENXIN (SG)
LYU WENXIN (SG)
Application Number:
PCT/SG2022/050711
Publication Date:
June 22, 2023
Filing Date:
October 05, 2022
Export Citation:
Assignee:
UNIV NANYANG TECH (SG)
International Classes:
C07H1/00; B01J31/02; B01J31/14; C07B41/12; C07D309/30; C07H15/04; C07H15/203; C07H15/26; C07H17/04; C07H23/00
Other References:
CRAMER, D. L. ET AL.: "Exploring Cooperative Effects in Oxidative NHC Catalysis: Regioselective Acylation of Carbohydrates", CHEMISTRY-A EUROPEAN JOURNAL, vol. 22, no. 22, 2 April 2016 (2016-04-02), pages 7403 - 7407, XP071879187, [retrieved on 20230526], DOI: 10.1002/CHEM.201601398
BLASZCZYK, S. A. ET AL.: "Recent advances in site-selective functionalization of carbohydrates mediated by organocatalysts", CARBOHYDRATE RESEARCH, vol. 471, 23 November 2018 (2018-11-23), pages 64 - 77, XP085560895, [retrieved on 20230526], DOI: 10.1016/J.CARRES. 2018.11.01 2
ROCHELEAU, S. ET AL.: "Highly Regioselective Monoacylation of Unprotected Glucopyranoside Using Transient Directing-Protecting Groups", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2017, no. 3, 29 November 2016 (2016-11-29), pages 646 - 656, XP072118534, [retrieved on 20230526], DOI: 10.1002/EJOC.201601457
LI REN-ZHE, TANG HUA, WAN LIQIANG, ZHANG XIA, FU ZHENGYAN, LIU JIE, YANG SHENGYONG, JIA DA, NIU DAWEN: "Site-Divergent Delivery of Terminal Propargyls to Carbohydrates by Synergistic Catalysis", CHEM, CELL PRESS, US, vol. 3, no. 5, 1 November 2017 (2017-11-01), US , pages 834 - 845, XP093076823, ISSN: 2451-9294, DOI: 10.1016/j.chempr.2017.09.007
LV WEN-XIN, CHEN HANG, ZHANG XINGLONG, HO CHANG CHIN, LIU YINGGUO, WU SHUQUAN, WANG HAIQI, JIN ZHICHAO, CHI YONGGUI ROBIN: "Programmable selective acylation of saccharides mediated by carbene and boronic acid", CHEM, CELL PRESS, US, vol. 8, no. 5, 1 May 2022 (2022-05-01), US , pages 1518 - 1534, XP093076824, ISSN: 2451-9294, DOI: 10.1016/j.chempr.2022.04.019
BLASZCZYK, S. A. ET AL.: "Recent advances in site-selective functionalization of carbohydrates mediated by organocatalysts", CARBOHYDRATE RESEARCH, vol. 471, 23 November 2018 (2018-11-23), pages 64 - 77, XP085560895, [retrieved on 20230526], DOI: 10.1016/J.CARRES. 2018.11.01 2
ROCHELEAU, S. ET AL.: "Highly Regioselective Monoacylation of Unprotected Glucopyranoside Using Transient Directing-Protecting Groups", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2017, no. 3, 29 November 2016 (2016-11-29), pages 646 - 656, XP072118534, [retrieved on 20230526], DOI: 10.1002/EJOC.201601457
LI REN-ZHE, TANG HUA, WAN LIQIANG, ZHANG XIA, FU ZHENGYAN, LIU JIE, YANG SHENGYONG, JIA DA, NIU DAWEN: "Site-Divergent Delivery of Terminal Propargyls to Carbohydrates by Synergistic Catalysis", CHEM, CELL PRESS, US, vol. 3, no. 5, 1 November 2017 (2017-11-01), US , pages 834 - 845, XP093076823, ISSN: 2451-9294, DOI: 10.1016/j.chempr.2017.09.007
LV WEN-XIN, CHEN HANG, ZHANG XINGLONG, HO CHANG CHIN, LIU YINGGUO, WU SHUQUAN, WANG HAIQI, JIN ZHICHAO, CHI YONGGUI ROBIN: "Programmable selective acylation of saccharides mediated by carbene and boronic acid", CHEM, CELL PRESS, US, vol. 8, no. 5, 1 May 2022 (2022-05-01), US , pages 1518 - 1534, XP093076824, ISSN: 2451-9294, DOI: 10.1016/j.chempr.2022.04.019
Attorney, Agent or Firm:
KINNAIRD, James Welsh (SG)
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