(S)-1-(三苯甲基氧代)戊-4-烯-2-醇 | 170277-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: (S)-1-(三苯甲基氧代)戊-4-烯-2-醇
• 英文名称: (2S)-1-triphenylmethoxy-4-pentene-2-ol
• 英文别名: (S)-1-trityloxypent-4-en-2-ol；(S)-1-(triphenylmethoxy)-4-penten-2-ol；4-Penten-2-ol, 1-(triphenylmethoxy)-, (2S)-；(2S)-1-trityloxypent-4-en-2-ol
• CAS: 170277-82-4
• 化学式: C₂₄H₂₄O₂
• 分子量: 344.453
• InChiKey: KDYRNYXQEPYCTD-QHCPKHFHSA-N

物化性质

• 沸点：
  482.7±33.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1-(三苯甲基氧代)戊-4-烯-2-醇 在 sodium hydroxide 、 sodium tetrahydroborate 、 sudan red 、 potassium tert-butylate 、 臭氧 作用下， 反应 13.75h， 生成 甲基三苯基甲基醚
  参考文献：
  名称：

  Macrocyclic Bisindolylmaleimides:  Synthesis by Inter- and Intramolecular Alkylation

  摘要：

  Macrocyclic bisindolylmaleimides 1-4 have been identified as competitive reversible inhibitors of PKC beta(1) and beta(2) and are being advanced to the clinic for evaluation as a treatment of retinopathy associated with diabetic complications. Highly convergent and stereoselective syntheses of 1-4 have been developed. The key synthetic step involves intermolecular alkylation of symmetrical bisindolylmaleimide 9 with chiral bisalkylating agent 8c and is amenable to the preparation of multikilogram quantities of these compounds. The synthetic sequence to 1, the most active compound, proceeds in 11 steps and 26% overall yield (>98% ee) from (R)-1-chloro-2,3-propanediol. No chromatographic purifications are required throughout the process and the final product is isolated in >97% purity after crystallization from DMF/MeOH. Synthesis of 1-4 by intramolecular alkylation proved less efficient, requiring 1? steps and affording 1-4 in lower overall yields of 6.0-8.5%.

  DOI：

  10.1021/jo971980h
• 作为产物：
  描述：

  (R)-3-chloro-1-O-trityl-1,2-propanediol 在 氢氧化钾 、 copper(l) iodide 作用下， 以 乙醇 为溶剂， 反应 1.25h， 生成 (S)-1-(三苯甲基氧代)戊-4-烯-2-醇
  参考文献：
  名称：

  Macrocyclic Bisindolylmaleimides:  Synthesis by Inter- and Intramolecular Alkylation

  摘要：

  Macrocyclic bisindolylmaleimides 1-4 have been identified as competitive reversible inhibitors of PKC beta(1) and beta(2) and are being advanced to the clinic for evaluation as a treatment of retinopathy associated with diabetic complications. Highly convergent and stereoselective syntheses of 1-4 have been developed. The key synthetic step involves intermolecular alkylation of symmetrical bisindolylmaleimide 9 with chiral bisalkylating agent 8c and is amenable to the preparation of multikilogram quantities of these compounds. The synthetic sequence to 1, the most active compound, proceeds in 11 steps and 26% overall yield (>98% ee) from (R)-1-chloro-2,3-propanediol. No chromatographic purifications are required throughout the process and the final product is isolated in >97% purity after crystallization from DMF/MeOH. Synthesis of 1-4 by intramolecular alkylation proved less efficient, requiring 1? steps and affording 1-4 in lower overall yields of 6.0-8.5%.

  DOI：

  10.1021/jo971980h

文献信息

• Total synthesis and absolute configuration of koshikalide
  作者：Kazuki Kunifuda、Arihiro Iwasaki、Masashi Nagamoto、Kiyotake Suenaga

  DOI：10.1016/j.tetlet.2016.06.002

  日期：2016.7

  koshikalide, a 14-membered macrolide that contains three olefins, was achieved. The skipped diene in the cyclic system was efficiently constructed by very mild Stille coupling at low temperature. The absolute stereochemistry was established by comparison of the specific optical rotations of natural and synthesized koshikalide.

  首次实现了全合成碱的合成，这是一种含有三种烯烃的14元大环内酯。通过在低温下进行非常温和的Stille偶联，可以有效地构建循环系统中跳过的二烯。通过比较天然和合成的koshikalide的特定旋光性，可以建立绝对立体化学。
• Synthesis of bisindolylmaleimides
  申请人：Eli Lilly and Company

  公开号：US05541347A1

  公开（公告）日：1996-07-30

  The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.

  本发明提供了一种新颖的合成方法，用于合成式(I)的化合物：##STR1## 这些化合物产量高，且无需使用昂贵的色谱分离。该合成方法特别有优势，因为它是立体选择性的。
• Total Synthesis of Sandramycin and Its Analogues via a Multicomponent Assemblage
  作者：Katsushi Katayama、Koji Nakagawa、Hiroshi Takeda、Akira Matsuda、Satoshi Ichikawa

  DOI：10.1021/ol403319m

  日期：2014.1.17

  The total synthesis of sandramycin has been accomplished by using a Staudinger/aza-Wittig/diastereoselective Ugi three-component reaction sequence as a key step to obtain a linear pentadepsipeptide. Subsequent [5 + 5] coupling of the penptapeptide, macrolactamization, and introduction of the quinaldin chromophores afforded sandramycin. Dihydroxy and diacetoxy analogues were also prepared, and the cytotoxic

  沙雷霉素的总合成已通过使用Staudinger / aza-Wittig / diastereoselective Ugi三组分反应序列作为获得线性五肽肽的关键步骤完成。随后五肽的[5 + 5]偶联，大内酰胺化和奎纳丁生色团的引入提供了沙雷霉素。还制备了二羟基和二乙酰氧基类似物，并评估了这些类似物对一系列人类癌细胞系的细胞毒活性。
• Synthesis and Characterization of the Selective, Reversible PKC_β Inhibitor (9<i>S</i>)-9-[(Dimethylamino)methyl]-6,7,10,11-tetrahydro-9<i>H</i>,18<i>H</i>-5,21:12,17-dimethenodibenzo[<i>e,k</i>]pyrrolo[3,4-<i>h</i>][1,4,13]oxadiazacyclohexadecine-18,20(19<i>H</i>)-dione, Ruboxistaurin (LY333531)
  作者：Anita H. Lewin、Larry Brieaddy、Jeffrey R. Deschamps、Gregory H. Imler、S. Wayne Mascarella、P. Anantha Reddy、F. Ivy Carroll

  DOI：10.1021/acschemneuro.8b00196

  日期：2019.1.16

  17-dimethenodibenzo[ e,k]pyrrolo[3,4- h][1,4,13]oxadiazacyclohexadecine-18,20(19 H)-dione, ruboxistaurin. Despite the interest in development of ruboxistaurin as the mesylate monohydrate (Arxxant) for the treatment of diabetic retinopathy, macular edema, and nephoropathy, several crucial details in physicochemical characterization were erroneous or missing. This report describes the synthesis and full characterization

  PKCβ在介导安非他明刺激的多巴胺流出中的调节作用，调节苯丙胺诱导的多巴胺转运蛋白的运输和活性，已证明促进了选择性可逆PKCβ抑制剂（9 S）-9-[（（二甲基氨基）甲基]- 6,7,10,11-四氢-9 H，18 H-5,21：12,17-二甲二苯并[e，k]吡咯并[3,4-h] [1,4,13]草二氮杂环十六烷-18,20 （19 H）-二酮，ruboxistaurin。尽管有兴趣开发鲁贝司他林作为甲磺酸盐一水合物（Arxxant）用于治疗糖尿病性视网膜病，黄斑水肿和肾病，但理化特性中的一些关键细节是错误的或缺失的。这份报告描述了Ruboxistaurin游离碱（作为一水合物）的合成和完整表征，包括X射线晶体学以确认其绝对构型，
• Intermediates for the synthesis of bisindolylmaleimides
  申请人：Eli Lilly and Company

  公开号：US05614647A1

  公开（公告）日：1997-03-25

  The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.

  本发明提供了一种新的合成公式(I)化合物的方法：##STR1## 该方法产率高且不需要使用昂贵的色谱分离技术。该合成方法尤其优越，因为它是立体选择性的。