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 | 460348-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 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
• 英文别名: methyl 2-[(E)-3-[(4S,5S)-5-[(Z,5R)-5-[tert-butyl(dimethyl)silyl]oxy-1-[(4-methoxyphenyl)methoxy]hex-2-enyl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-1-enyl]-6-hydroxy-4-methoxybenzoate
• CAS: 460348-32-7
• 化学式: C₃₇H₅₄O₉Si
• 分子量: 670.916
• InChiKey: JBGODUZIHPODNQ-WPLJTPORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.06
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  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 在 sodium hydroxide 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 6.0h， 生成 2-Hydroxy-6-((E)-3-{(4S,5S)-5-[(Z)-(R)-5-hydroxy-1-(4-methoxy-benzyloxy)-hex-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-propenyl)-4-methoxy-benzoic acid
  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：

  4-甲氧基水杨酸 在 叔丁基锂 、 二(3-甲基丁烷-2-基)硼烷 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 19.17h， 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

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.