CAS: 127943-53-7; Discodermolide

该化合物是天然产品,最初与海绵分离,但与海洋海绵分解不相容,是一种复杂的巨体,其独特的结构是大型乳内酮环和多立体分解器,有助于其风性.该复合物显示出重要的生物活动,特别是抗脉冲剂,稳定微孔和干扰正常细胞分解,类似于帕利塔克斯行动机制.其潜在的治疗用途引起了癌症研究的兴趣.(+)-Discodolmolid通常是一种白色到白色的固体,在二甲基硫氧化物(DMSO)和乙醇等有机溶剂中可溶解,但水溶性有限.该复合物的合成和提取可能因其复杂的结构而具有挑战性,导致对更有效的生产方法的持续研究.

结构式图片

MSDS等安全信息

    上下游产品

    (+)-Discodermolide
    3,11,17-O-Tris-(Tert-Butyldimethylsilyl)Discodermolide 261968-27-8
    [(3Z,5S,6S,7R,8R,9S,11Z,13S,14S,15S,16Z,18S)-8,14,18-Tris[[tert-Butyl(Dimethyl)Silyl]Oxy]-19-[(2S,3S,4S,5R)-4-[tert-Butyl(Dimethyl)Silyl]Oxy-3,5-Dimethyl-6-Oxooxan-2-Yl]-5,7,9,11,13,15-Hexamethylnonadeca-1,3,11,16-Tetraen-6-Yl] Carbamate 252342-55-5
    Methyl (2R,3S,4S,5S,7S,8Z,10S,11S,12S,13Z,16S,17R,18S,19S,20S,21Z)-3,11,17-Tris-(T-Butyldimethylsilyloxy)-5,7-Dihydroxy-19-(Carbamoyloxy)-2,4,10,12,14,16,18,20-Octamethyl-Tetracosa-8,13,21,23-Tetraenoate 261968-26-7
    11,17-Bis-(T-Butyldimethylsilyl)-3-Triethylsilyl-7-Oxo-Discodermolide 827603-12-3
    Methyl (2R,3S,4S,5S,8Z,10S,11S,12S,13Z,16S,17R,18R,19S,20S,21Z)-5-[tert-Butyl(Dimethyl)Silyl]Oxy-19-Carbamoyloxy-7-Hydroxy-2,4,10,12,14,16,18,20-Octamethyl-3,11,17-Tris[tri(Propan-2-yl)Silyloxy]Tetracosa-8,13,21,23-Tetraenoate 600737-60-8
    (3R,4S,5S,6S)-4-[tert-Butyl(Dimethyl)Silyl]Oxy-3,5-Dimethyl-6-[(2S,3Z,5S,6S,7S,8Z,11S,12R,13R,14S,15S,16Z)-2,6,12-Tris[[tert-Butyl(Dimethyl)Silyl]Oxy]-14-Hydroxy-5,7,9,11,13,15-Hexamethylnonadeca-3,8,16,18-Tetraenyl]Oxan-2-One 252342-48-6
    Methyl (2R,3S,4R,7S,8Z,10S,11S,12S,13Z,16S,17R,18S,19S,20S,21Z)-3,11,17-Tris-(T-Butyldimethylsilyloxy)-19-(Carbamoyloxy)-7-Hydroxy-2,4,10,12,14,16,18,20-Octamethyl-5-Oxo-Tetracosa-8,13,21,23-Tetraenoate 261968-25-6 Carbamic Acid (6Z,11Z)-(1S,2R,3R,4S,8S,9S,10S)-3,9-Bis(Tert-Butyldimethylsilanyloxy)-2,4,6,8,10-Pentamethyl-1-((Z)-(S)-1-Methylpenta-2,4-Dienyl)-13-Oxo-Trideca-6,11-Dienyl Ester 261968-08-5 (3R,4S,5S,6S)-4-[tert-Butyl(Dimethyl)Silyl]Oxy-3,5-Dimethyl-6-[(2S,3Z,5S,6S,7S,8Z,11S,12R,13R,14S,15S,16Z)-2,6,12-Tris[[tert-Butyl(Dimethyl)Silyl]Oxy]-14-[(4-Methoxyphenyl)Methoxy]-5,7,9,11,13,15-Hexamethylnonadeca-3,8,16,18-Tetraenyl]Oxan-2-One 252342-47-5

    合成工艺路线路线简述

      📜[(1Z,3S,4R,5S,6Z,9S,10R,11R,12S,13S)-1-Iodo-12-(Methoxymethoxy)-14-[(4-Methoxyphenyl)Methoxy]-3,5,7,9,11,13-Hexamethyl-10-Tri(Propan-2-yl)Silyloxytetradeca-1,6-Dien-4-Yl]Oxy-Tri(Propan-2-yl)Silane置于chromium Dichloride,Aluminum Oxide,N-甲基吲哚酮,四丙基高钌酸铵,(-)-Chiral Bispyridinyl-Based Ligand,4 A Molecular Sieve,氢氟酸,Potassium Hydride,乙酰氯,2,3-二氯-5,6-二氰基-1,4-苯醌,Nickel Dichloride体系中,用 四氢呋喃,乙醇,正己烷,二氯甲烷,水,甲苯,乙腈,苯 用作溶剂,化学反应 229.72H,反应生成盘皮海绵内酯
      参考文献:有效的微管稳定剂(+)-Discodermolide的全合成.
      标题:有效的微管稳定剂(+)-Discodermolide的全合成.
      摘要:描述了有效的稳定微管,抗有丝分裂剂(+)-Discodermolide的全合成.收敛的合成策略利用了酮烯酸酯的非对映选择性烷基化来建立关键的c15-C16键.该合成适合制备克级量的(+)-Discodermolide及其类似物.
      Doi:10.1021/jo034521R

      海关参考信息

      专利信息


      专利号:US-2004018598-A1
      优先权日:2000-05-30
      标题 :Bio-intermediates for use in the chemical synthesis of polyketides
      发明人:SANTI DANIEL; ASHLEY GARY; MYLES DAVID C
      摘要:The present invention relates to compounds made by a subset of modules from one or more polyketide synthase (“PKSâ€?) genes that are used as starting material in the chemical synthesis of novel molecules, particularly naturally occurring polyketides or derivatives thereof. The biologically derived intermediates (“bio-intermediatesâ€?) generally represent particularly difficult compounds to synthesize using traditional chemical approaches due to one or more stereocenters. In one aspect of the invention, an intermediate in the synthesis of epothilone is provided that feeds into the synthetic protocol of Danishefsky and co-workers. In another aspect of the invention, intermediates in the synthesis of discodermolide are provided that feed into the synthetic protocol of Smith and co-workers. By taking advantage of the inherent stereochemical specificity of biological processes, the syntheses of key intermediates and thus the overall syntheses of compounds like epothilone and discodermolide are greaty simplified.

      专利号:US-2012177593-A1
      优先权日:2009-07-20
      标 题 :Synthesis of dendrimer conjugates
      发明人:BAKER JR JAMES R; ZHANG YUEHUA; THOMAS THOMMEY P; DESAI ANKUR MAHESH
      权利人:BAKER JR JAMES R; ZHANG YUEHUA; THOMAS THOMMEY P; DESAI ANKUR MAHESH; UNIV MICHIGAN
      摘要:The present invention relates to novel methods of synthesis of therapeutic and diagnostic dendrimers. In particular, the present invention is directed to novel dendrimer conjugates, novel methods of synthesizing the same, compositions comprising the conjugates, as well as systems and methods utilizing the conjugates (e.g., in diagnostic and/or therapeutic settings (e.g., for the delivery of therapeutics, imaging, and/or targeting agents (e.g., in disease (e.g., cancer, inflammatory disease) diagnosis and/or therapy, pain therapy, etc.)). Accordingly, dendrimer conjugates of the present invention may further comprise at least two different components for targeting, imaging, sensing, and/or providing a therapeutic or diagnostic material and/or monitoring response to therapy. Furthermore, the novel synthesis methods of certain embodiments of the present invention provide significant advantages with regard to total reaction time and simplicity.

      专利号:US-10973847-B2
      优先权日:2017-06-30
      标题 :Core-to-surface polymerization for the synthesis of star polymers and uses thereof
      发明人:JOHNSON JEREMIAH A; GOLDER MATTHEW R
      权利人:MASSACHUSETTS INST TECHNOLOGY
      摘要:Disclosed are methods, compositions, reagents, systems, and kits to prepare star polymers, as well as compositions and uses thereof. Various embodiments show that synthesis of these polymers contain low metal concentration to provide polymers for diverse biomedical applications including in vivo applications.

      专利号:US-7348436-B2
      优先权日:2004-03-02
      标题 :Compounds useful for the synthesis of (+)-discodermolide and methods thereof
      发明人:MYLES DAVID C; SHAW SIMON JAMES; SUNDERMANN KURT F
      权利人:KOSAN BIOSCIENCES INC
      摘要:Compounds and methods useful for the synthesis of (+)-discodermolide, a naturally occurring microtubule stabilizing agent useful as an anti-cancer agent.

      专利号:US-12391691-B2
      优先权日:2018-11-16
      标题:Synthesis of key intermediate of KRAS G12C inhibitor compound
      发明人:PARSONS ANDREW THOMAS; COCHRAN BRIAN MCNEIL; POWAZINIK IV WILLIAM; CAPORINI MARC ANTHONY
      权利人:AMGEN INC
      摘要:The present invention relates to an improved, efficient, scalable process to prepare intermediate compounds, such as compound 5M, having the structure n nuseful for the synthesis of compounds that target KRAS G12C mutations, such as

      专利号:US-2025206736-A1
      优先权日:2019-11-14
      标题 :Synthesis of kras g12c inhibitor compound
      发明人:CORBETT MICHAEL THOMAS; CAILLE SEBASTIEN
      权利人:AMGEN INC
      摘要:The present disclosure relates to an improved, efficient, scalable process to prepare intermediate compounds, such as 2-isopropyl-4-methylpyridin-3-amine, useful for the synthesis of compounds, such as Compound 9, for the treatment of KRAS G12C mutated cancers.

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      品牌试剂参考报价(招募中)

      📌 第三方产品分析报告

      ✅ COA系统入驻 | 共享模式

      主要参考文献


      1: Terwilliger DW, Trauner D. Selective Synthesis of Divergolide I. J Am Chem Soc. 2018 Feb 28;140(8):2748-2751. doi: 10.1021/jacs.7b13092. Epub 2018 Feb 15. doi: 10.1039/c4ob02244k. doi: 10.1002/cbic.201402071. Epub 2014 May 27. doi: 10.1016/j.gene.2014.04.052. Epub 2014 Apr 24. doi: 10.1021/ol5003847. Epub 2014 Mar 25. doi: 10.1021/ol400528g. Epub 2013 Mar 25.

      合成参考文献


      参考文献:10.1007/978-1-61779-252-6_18
      摘要:Honore S, Braguer D. Investigating microtubule dynamic instability using microtubule-targeting agents. Methods Mol Biol. 2011;777():245–60. doi: 10.1007/978-1-61779-252-6_18.
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