(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-[(4R,5S)-2,2-dimethyl-5-(3-trimethylsilanyl-prop-2-ynyl)-[1,3]dioxolan-4-yl]-hex-2-en-1-ol | 460348-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-[(4R,5S)-2,2-dimethyl-5-(3-trimethylsilanyl-prop-2-ynyl)-[1,3]dioxolan-4-yl]-hex-2-en-1-ol
• 英文别名: (Z,5R)-5-[tert-butyl(dimethyl)silyl]oxy-1-[(4R,5S)-2,2-dimethyl-5-(3-trimethylsilylprop-2-ynyl)-1,3-dioxolan-4-yl]hex-2-en-1-ol
• CAS: 460348-28-1
• 化学式: C₂₃H₄₄O₄Si₂
• 分子量: 440.771
• InChiKey: CCWUSAVMYPRQLQ-PIVKVPAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-[(4R,5S)-2,2-dimethyl-5-(3-trimethylsilanyl-prop-2-ynyl)-[1,3]dioxolan-4-yl]-hex-2-en-1-ol 在 二(3-甲基丁烷-2-基)硼烷 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 19.0h， 生成 2-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-6-hydroxy-4-methoxy-benzoic acid methyl ester
  参考文献：
  名称：

  Convergent stereospecific synthesis of C292 (or LL-Z1640-2), and hypothemycin. Part 1

  摘要：

  The stereospecific synthesis of the precursors required for the 14-membered ring formation either via an intramolecular Suzuki coupling or via an intermolecular Suzuki coupling followed by a macrolactonisation is herein reported. One-pot Suzuki couplings were here achieved with vinyldisiamylboranes which were generated in situ from the related chiral precursor. The present convergent approach of C292 (or LL-21640-2) and hypothemycin gives a flexible access to related macrolides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00870-5
• 作为产物：
  描述：

  (R)-5-(trimethylsilyl)pent-4-yn-2-ol 在 咪唑 、 正丁基锂 、 叔丁基锂 、 二(3-甲基丁烷-2-基)硼烷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 11.5h， 生成 (Z)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-[(4R,5S)-2,2-dimethyl-5-(3-trimethylsilanyl-prop-2-ynyl)-[1,3]dioxolan-4-yl]-hex-2-en-1-ol
  参考文献：
  名称：

  Convergent stereospecific synthesis of C292 (or LL-Z1640-2), and hypothemycin. Part 1

  摘要：

  The stereospecific synthesis of the precursors required for the 14-membered ring formation either via an intramolecular Suzuki coupling or via an intermolecular Suzuki coupling followed by a macrolactonisation is herein reported. One-pot Suzuki couplings were here achieved with vinyldisiamylboranes which were generated in situ from the related chiral precursor. The present convergent approach of C292 (or LL-21640-2) and hypothemycin gives a flexible access to related macrolides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00870-5

文献信息

• Convergent stereospecific synthesis of C292 (or LL-Z1640-2), and hypothemycin. Part 1
  作者：Patrice Sellès、Robert Lett

  DOI：10.1016/s0040-4039(02)00870-5

  日期：2002.5

  The stereospecific synthesis of the precursors required for the 14-membered ring formation either via an intramolecular Suzuki coupling or via an intermolecular Suzuki coupling followed by a macrolactonisation is herein reported. One-pot Suzuki couplings were here achieved with vinyldisiamylboranes which were generated in situ from the related chiral precursor. The present convergent approach of C292 (or LL-21640-2) and hypothemycin gives a flexible access to related macrolides. (C) 2002 Elsevier Science Ltd. All rights reserved.