(R)-(6-(benzyloxy)-2,5,7,8-tetramethylchroman-2-yl)methyl trifluoromethane-sulfonate | 479353-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (R)-(6-(benzyloxy)-2,5,7,8-tetramethylchroman-2-yl)methyl trifluoromethane-sulfonate
• 英文别名: [(2R)-2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl]methyl trifluoromethanesulfonate
• CAS: 479353-40-7
• 化学式: C₂₂H₂₅F₃O₅S
• 分子量: 458.499
• InChiKey: DWUCNLZCHGTAID-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-(6-(benzyloxy)-2,5,7,8-tetramethylchroman-2-yl)methyl trifluoromethane-sulfonate 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 正丁基锂 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 反应 0.5h， 生成 (S,E)-6-(benzyloxy)-2-(4,8-dimethylnona-3,7-dien-1-yl)-2,5,7,8-tetramethyl-chromane
  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 sodium tetrahydroborate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 41.5h， 生成 (R)-(6-(benzyloxy)-2,5,7,8-tetramethylchroman-2-yl)methyl trifluoromethane-sulfonate
  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

• A Simple¹³C NMR Method for the Discrimination of Complex Mixtures of Stereoisomers: All Eight Stereoisomers of α-Tocopherol Resolved
  作者：Peter P. Lankhorst、Thomas Netscher、Alexander L. L. Duchateau

  DOI：10.1002/chir.22535

  日期：2015.11

  A simple one‐dimensional 13C NMR method is presented to discriminate between stereoisomers of organic compounds with more than one chiral center. By means of this method it is possible to discriminate between all eight stereoisomers of α‐tocopherol. To achieve this the chiral solvating agent (S)‐(+)‐1‐(9‐anthryl)‐2,2,2‐trifluoroethanol and the compound of interest were dissolved in high concentrations

  提出了一种简单的一维13 C NMR方法来区分具有一个以上手性中心的有机化合物的立体异构体。通过这种方法，可以区分α-生育酚的所有八个立体异构体。为此，将手性溶剂化剂（S）-（+）-1-（9-蒽基）-2,2,2-三氟乙醇和目标化合物高浓度溶解于氯仿-d中，并进行核磁共振（NMR）光谱是在低温下记录的。α-生育酚的各个立体异构体由参考化合物的加标峰指定。该方法还应用于其他六个代表性示例。手性27：850–855，2015。©2015 Wiley Periodicals，Inc.
• 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.
• CHINONE-, HYDROCHINOME- AND NAPHTHOCHINONE-ANALOGUES OF VATIQUIONE FOR TREATMENT OF MITOCHONDRIAL DISORDER DISEASES
  申请人：Stealth BioTherapeutics Inc.

  公开号：EP4038076A1

  公开（公告）日：2022-08-10
• 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)).