(S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxypent-4-en-1-one | 1205666-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxypent-4-en-1-one
• 英文别名: (S)-1-[(R)-4-benzyl-2-thioxothiazolidin-3-yl]-3-hydroxypent-4-en-1-one；(3S)-1-[(4R)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-hydroxypent-4-en-1-one
• CAS: 1205666-47-2
• 化学式: C₁₅H₁₇NO₂S₂
• 分子量: 307.437
• InChiKey: ZDRXMXDZHDOUPU-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxypent-4-en-1-one 在 咪唑 、 4-二甲氨基吡啶 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 26.0h， 生成 (2R,4S)-4-[(tert-butyldiphenylsilyl)oxy]hex-5-en-2-yl (S)-4-[(tert-butyldiphenylsilyl)oxy]hex-5-enoate
  参考文献：
  名称：

  Stereoselective total synthesis of stagonolide-C

  摘要：

  The highly stereoselective synthesis of a biologically active stagonolide-C has been described. The pivotal functionalities are derived from Barbier allylation, an epoxidation by m-CPBA, a chiral-auxiliary mediated acetate aldol addition, a 1,3-anti-reduction, a Sharpless kinetic resolution, a Yamaguchi macrolactonization, and ring-closing metathesis. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.015
• 作为产物：
  描述：

  (R)-4-苄基噻唑啉-2-硫酮 在 正丁基锂 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.08h， 生成 (S)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxypent-4-en-1-one 、 (R)-1-((R)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxypent-4-en-1-one
  参考文献：
  名称：

  Stereoselective total synthesis of stagonolide-C

  摘要：

  The highly stereoselective synthesis of a biologically active stagonolide-C has been described. The pivotal functionalities are derived from Barbier allylation, an epoxidation by m-CPBA, a chiral-auxiliary mediated acetate aldol addition, a 1,3-anti-reduction, a Sharpless kinetic resolution, a Yamaguchi macrolactonization, and ring-closing metathesis. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.015

文献信息

• Method for preparing largazole analogs and uses thereof
  申请人：Williams Robert M.

  公开号：US20100029731A1

  公开（公告）日：2010-02-04

  Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.

  本文描述了类似largazole的类似物。此外，还描述了使用largazole和largazole类似物治疗癌症和血液疾病的方法，以及包含它们的药物组合物。同样描述了制备largazole类似物的方法。
• [EN] METHOD FOR PREPARING LARGAZOLE ANALOGS AND USES THEREOF<br/>[FR] PROCÉDÉ DE PRÉPARATION DE PARTICULES CREUSES ET LEURS UTILISATIONS
  申请人：UNIV COLORADO STATE RES FOUND

  公开号：WO2016144665A1

  公开（公告）日：2016-09-15

  Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.

  本文描述了类似largazole的类似物。此外，还描述了使用largazole和largazole类似物治疗癌症和血液疾病的方法，以及包含它们的药物组合物。同样描述了制备largazole类似物的方法。
• The stereoselective total synthesis of (−)-achaetolide
  作者：Pallavi Thakur、Boyapelly Kumaraswamy、Gurram Raji Reddy、Rakeshwar Bandichhor、Khagga Mukkantii

  DOI：10.1016/j.tetasy.2012.03.010

  日期：2012.4

  The stereoselective total synthesis of (-)-achaetolide is described in a convergent manner. Grignard addition, Wittig homologation, acetate aldol and ring closing metathesis reactions were the key steps involved. The required olefinic alcohol fragments were synthesized from a single chiral pool material 2-deoxy-D-ribose and olefinic acid fragment was prepared from acetate aldol reaction. Both the olefinic acid and alcohols were prepared in a concise method. (C) 2012 Elsevier Ltd. All rights reserved.
• Method for Preparing Largazole Analogs and Uses Thereof
  申请人：Williams Robert M.

  公开号：US20120264794A1

  公开（公告）日：2012-10-18

  Analogs of largazole are described herein. Methods of treating cancer and blood disorders using largazole and largazole analogs and pharmaceutical compositions comprising the same are additionally described herein. Methods for preparing largazole analogs are likewise described.
• US8217076B2
  申请人：——

  公开号：US8217076B2

  公开（公告）日：2012-07-10