(R)-1-(2-((S)-2-(tert-butyldimethylsilyloxy)propyl)-1,3-dithian-2-yl)pent-4-en-2-ol | 1147012-65-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (R)-1-(2-((S)-2-(tert-butyldimethylsilyloxy)propyl)-1,3-dithian-2-yl)pent-4-en-2-ol
• 英文别名: (2R)-1-[2-[(2S)-2-[tert-butyl(dimethyl)silyl]oxypropyl]-1,3-dithian-2-yl]pent-4-en-2-ol
• CAS: 1147012-65-4
• 化学式: C₁₈H₃₆O₂S₂Si
• 分子量: 376.7
• InChiKey: KJWIDDPTOZKSFO-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.68
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  80.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1-(2-((S)-2-(tert-butyldimethylsilyloxy)propyl)-1,3-dithian-2-yl)pent-4-en-2-ol 在 吡啶 、 Hoveyda-Grubbs catalyst second generation 、 茴香硫醚 、 二乙基甲氧基硼烷 、 水 、 N,N-二异丙基乙胺 、 三氟乙酸 、 calcium carbonate 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 13.17h， 生成 (+)-cryptocarya diacetate
  参考文献：
  名称：

  A Unified Synthetic Strategy to the Cryptocarya Family of Natural Products Exploiting Anion Relay Chemistry (ARC)

  摘要：

  A unified synthetic strategy to the Cryptocarya family of natural products has been achieved employing four-component fragment unions in a "single flask" exploiting Anion Relay Chemistry (ARC). Functionalization of the ARC adducts permits rapid construction of five polyhydroxylated di- and tetrahydropyrone natural products of the Cryptocarya class (1-5), in a total of 7-9 steps from commercially available materials.

  DOI：

  10.1021/ol400857k
• 作为产物：
  描述：

  2-(叔丁基二甲基甲硅烷基)-1,3-二噻烷 在 正丁基锂 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 5.16h， 生成 (R)-1-(2-((S)-2-(tert-butyldimethylsilyloxy)propyl)-1,3-dithian-2-yl)pent-4-en-2-ol
  参考文献：
  名称：

  A Unified Synthetic Strategy to the Cryptocarya Family of Natural Products Exploiting Anion Relay Chemistry (ARC)

  摘要：

  A unified synthetic strategy to the Cryptocarya family of natural products has been achieved employing four-component fragment unions in a "single flask" exploiting Anion Relay Chemistry (ARC). Functionalization of the ARC adducts permits rapid construction of five polyhydroxylated di- and tetrahydropyrone natural products of the Cryptocarya class (1-5), in a total of 7-9 steps from commercially available materials.

  DOI：

  10.1021/ol400857k

文献信息

• A Short Total Synthesis of (+)-Cryptocarya Diacetate
  作者：Mukund K. Gurjar、Neelarapu Raghupathi、Mukund S. Chorghade

  DOI：10.3987/com-08-s(f)107

  日期：——

  A short synthesis of (+)-cryptocarya diacetate was achieved by employing three component linchpin coupling, diastereoselective reduction of β-hydroxyketone, and Z-selective HWE reaction as key transformations.

  通过采用三组分关键偶联、β-羟基酮的非对映选择性还原和 Z-选择性 HWE 反应作为关键转化，实现了 (+)-二乙酸隐核糖酯的短合成。
• A Unified Synthetic Strategy to the Cryptocarya Family of Natural Products Exploiting Anion Relay Chemistry (ARC)
  作者：Bruno Melillo、Amos B. Smith

  DOI：10.1021/ol400857k

  日期：2013.5.3

  A unified synthetic strategy to the Cryptocarya family of natural products has been achieved employing four-component fragment unions in a "single flask" exploiting Anion Relay Chemistry (ARC). Functionalization of the ARC adducts permits rapid construction of five polyhydroxylated di- and tetrahydropyrone natural products of the Cryptocarya class (1-5), in a total of 7-9 steps from commercially available materials.