(Z)-(R)-2-Methyl-4-triisopropylsilanyloxymethyl-hex-2-en-1-ol | 645386-92-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-(R)-2-Methyl-4-triisopropylsilanyloxymethyl-hex-2-en-1-ol
• 英文别名: (Z,4R)-2-methyl-4-[tri(propan-2-yl)silyloxymethyl]hex-2-en-1-ol
• CAS: 645386-92-1
• 化学式: C₁₇H₃₆O₂Si
• 分子量: 300.557
• InChiKey: NKBHVXABDFOUJP-LPPOOGIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (Z)-(R)-2-Methyl-4-triisopropylsilanyloxymethyl-hex-2-en-1-ol 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4R,5Z,7R)-5-methyl-7-[tri(propan-2-yl)silyloxymethyl]nona-1,5-dien-4-ol
  参考文献：
  名称：

  Toward a Total Synthesis of Peloruside A:  Enantioselective Preparation of the C8−C19 Region

  摘要：

  [GRAPHICS]An efficient synthetic sequence toward the C8-C19 region of peloruside A has been developed. The route is highlighted by a selective electrophilic cyclization reaction, a single-step epoxide ring-opening/methylation sequence, and a stereoselective Mukaiyama aldol reaction.

  DOI：

  10.1021/ol0358814
• 作为产物：
  描述：

  (R)-2-Triisopropylsilanyloxymethyl-butan-1-ol 在 吡啶 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 (Z)-(R)-2-Methyl-4-triisopropylsilanyloxymethyl-hex-2-en-1-ol
  参考文献：
  名称：

  Toward a Total Synthesis of Peloruside A:  Enantioselective Preparation of the C8−C19 Region

  摘要：

  [GRAPHICS]An efficient synthetic sequence toward the C8-C19 region of peloruside A has been developed. The route is highlighted by a selective electrophilic cyclization reaction, a single-step epoxide ring-opening/methylation sequence, and a stereoselective Mukaiyama aldol reaction.

  DOI：

  10.1021/ol0358814

文献信息

• Function-Oriented Synthesis toward Peloruside A Analogues
  作者：Anne-Caroline Chany、Frédéric Legros、Heloua Haroun、Uday Kumar Kundu、Bohdan Biletskyi、Sergii Torlak、Monique Mathé-Allainmat、Jacques Lebreton、Aurélie Macé、Bertrand Carboni、Brigitte Renoux、Pascal Gosselin、Gilles Dujardin、Catherine Gaulon-Nourry

  DOI：10.1021/acs.orglett.9b00413

  日期：2019.5.3

  A convergent and rapid synthesis of original C2,C3-unsaturated, C11,C13-keto–enol macrocycles with a peloruside A skeleton has been developed. These original unsaturated macrocycles constitute valuable platforms to access peloruside A analogues with high diversity. The four-fragment strategy implemented features two aldol-type couplings with the central C12–C14 building block TES-diazoacetone and a

  已经开发了一种融合和快速合成原始的C2，C3不饱和，C11，C13-酮-烯醇大环化合物，并具有蛇绿苷A骨架的方法。这些原始的不饱和大环化合物构成了有价值的平台，可用于获得高度多样性的鹅膏苷A类似物。实施的四段式策略具有两个醛醇型偶联剂，与中央C12–C14构造单元TES-重氮丙酮和晚期闭环复分解反应。Enantiopure类似物18ab对NCI和MCF7肿瘤细胞系具有低微摩尔范围的抗增殖活性。
• A stereoselective synthesis of the C11–C19 fragment of (+)-peloruside A
  作者：Zhen-liang Chen、Wei-shan Zhou

  DOI：10.1016/j.tetlet.2006.05.135

  日期：2006.7

  A new route to the synthesis of the C I I-C 19 fragment of peloruside A is described, which includes an aldol reaction with ethyl acetoacetate, P-hydroxyl-directed reduction of P-hydroxy ketone, as well as methylation of C 13 hydroxyl moiety in the system of Mel-Ag2O-MgSO4-CH2Cl2. (c) 2006 Elsevier Ltd. All rights reserved.
• Toward a Total Synthesis of Peloruside A:  Enantioselective Preparation of the C8−C19 Region
  作者：Richard E. Taylor、Meizhong Jin

  DOI：10.1021/ol0358814

  日期：2003.12.1

  [GRAPHICS]An efficient synthetic sequence toward the C8-C19 region of peloruside A has been developed. The route is highlighted by a selective electrophilic cyclization reaction, a single-step epoxide ring-opening/methylation sequence, and a stereoselective Mukaiyama aldol reaction.