(2R)-6-(benzyloxy)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyl-2-(phenylsulfonyl)trideca-3,7,11-trien-1-yl)chromane | 479353-41-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R)-6-(benzyloxy)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyl-2-(phenylsulfonyl)trideca-3,7,11-trien-1-yl)chromane
• 英文别名: (2R)-2-[(3E,7E)-2-(benzenesulfonyl)-4,8,12-trimethyltrideca-3,7,11-trienyl]-2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromene
• CAS: 479353-41-8
• 化学式: C₄₂H₅₄O₄S
• 分子量: 654.954
• InChiKey: RZTAGHVDGBPHAL-QIFGFZMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  47
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-6-(benzyloxy)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyl-2-(phenylsulfonyl)trideca-3,7,11-trien-1-yl)chromane 在 正丙胺 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 lithium 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (S)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)chroman-6-ol
  参考文献：
  名称：

  [EN] COMPOUNDS, COMPOSITIONS AND METHODS FOR THE PREVENTION AND/OR TREATMENT OF VARIOUS MITOCHONDRIAL DISEASES OR DISORDERS, INCLUDING FRIEDREICH'S ATAXIA
  [FR] COMPOSÉS, COMPOSITIONS ET PROCÉDÉS POUR LA PRÉVENTION ET/OU LE TRAITEMENT DE DIVERSES MALADIES OU TROUBLES MITOCHONDRIAUX, NOTAMMENT LA MALADIE DE FRIEDREICH

  摘要：

  该披露提供了各种新的和现有的化合物，可单独使用或作为组合物（例如药物）中的成分，并提供了用于治疗、预防、抑制、改善或延迟哺乳动物主体中与铁死亡相关的疾病、疾病或疾病的发作的相关方法和用途。这种与铁死亡相关的疾病、疾病或疾病可以包括：弗里德雷希共济失调、利氏综合征、勒伯遗传性视神经病变（LHON）、（增殖性、非增殖性、糖尿病或高血压）视网膜病变、难治性癫痫、帕金森病（PD）、阿尔茨海默病（AD）、亨廷顿病（HD）、肌萎缩性侧索硬化症（ALS）、缺血性中风、心肌病（例如心脏缺血再灌注损伤、心肌梗塞、巴斯心肌病、肥厚型心肌病或心力衰竭）、肾损伤、肾缺血再灌注损伤或急性肾衰竭。

  公开号：

  WO2022261347A1
• 作为产物：
  描述：

  [(2S)-6-hydroxy-2-(hydroxymethyl)-5,7,8-trimethyl-3,4-dihydrochromen-2-yl]methyl acetate 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 正丁基锂 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 60.0h， 生成 (2R)-6-(benzyloxy)-2,5,7,8-tetramethyl-2-((3E,7E)-4,8,12-trimethyl-2-(phenylsulfonyl)trideca-3,7,11-trien-1-yl)chromane
  参考文献：
  名称：

  Chemoenzymatic synthesis of both enantiomers of α-tocotrienol

  摘要：

  The stereoselective acylation of the achiral chromanedimethanol derivative 1 by vinyl acetate in the presence of Candida antarctica lipase B gave the (S)-monoester 2 in high enantiomeric purity (ee >= 98%). Enzymatic hydrolysis of diesters of compound I failed to give (R)-monoester 2 in good yield and high ee. Thus, both enantiomers of alpha-tocotrienol were synthesized from the (S)-monoester 2. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.035

文献信息

• WO2021067836A5
  申请人：——

  公开号：WO2021067836A5

  公开（公告）日：2024-03-28
• Synthesis of (S)-α-tocotrienol via an enzymatic desymmetrization of an achiral chroman derivative
  作者：Robert Chênevert、Gabriel Courchesne

  DOI：10.1016/s0040-4039(02)01865-8

  日期：2002.10

  The stereoselective acylation of an achiral chromandimethanol derivative by vinyl acetate in the presence of Candida antarctica lipase in organic media gave the corresponding (S)-monoester in high enantiomeric purity (ee=98%). (S)-alpha-Tocotrienol was synthesized in 19% overall yield over six steps from this (S)-monoester. (C) 2002 Elsevier Science Ltd. All rights reserved.
• COMPOSITIONS AND METHODS FOR THE PREVENTION AND/OR TREATMENT OF MITOCHONDRIAL DISEASE, INCLUDING FRIEDREICH'S ATAXIA
  申请人：Keefe Dennis

  公开号：US20210206736A1

  公开（公告）日：2021-07-08

  The disclosure provides therapeutic compositions (i.e., therapeutic agents) and methods of preventing or treating Friedreich's ataxia in a mammalian subject, reducing risk factors, signs and/or symptoms associated with Friedreich's ataxia (e.g., Complex I deficiency), and/or reducing the likelihood or severity of Friedreich's ataxia. The disclosure further provides novel intermediates for the production of said therapeutic compositions and related reduced versions of said therapeutic compositions, which reduce forms may also be used as therapeutic agents (or prodrugs of the therapeutic agent(s)).
• [EN] CHINONE-, HYDROCHINOME- AND NAPHTHOCHINONE-ANALOGUES OF VATIQUIONE FOR TREATMENT OF MITOCHONDRIAL DISORDER DISEASES<br/>[FR] ANALOGUES CHINONE, HYDROCHINONE ET NAPHTOCHINONE DE VATIQUINONE POUR LE TRAITEMENT DE MALADIES À TROUBLES MITOCHONDRIAUX
  申请人：STEALTH BIOTHERAPEUTICS CORP

  公开号：WO2021067836A1

  公开（公告）日：2021-04-08

  The disclosure provides therapeutic compositions (i.e., therapeutic agents) and methods of preventing or treating Friedreich's ataxia in a mammalian subject, reducing risk factors, signs and/or symptoms associated with Friedreich's ataxia (e.g. Complex I deficiency), and/or reducing the likelihood or severity of Friedreich's ataxia. The disclosure further provides novel intermediates for the production of said therapeutic compositions and related reduced versions of said therapeutic compositions, which reduce forms may also be used as therapeutic agents (or prodrugs of the therapeutic agent(s)).