(3R,4R,6Z,8S,9R,10R,11S)-4,8-bis[[tert-butyl(dimethyl)silyl]oxy]-13-[tert-butyl(diphenyl)silyl]oxy-9-[(4-methoxyphenyl)methoxy]-10,11-dimethyl-2-[(2S,5S)-5-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxolan-2-yl]trideca-1,6-dien-3-ol | 1195988-08-9

• 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: (3R,4R,6Z,8S,9R,10R,11S)-4,8-bis[[tert-butyl(dimethyl)silyl]oxy]-13-[tert-butyl(diphenyl)silyl]oxy-9-[(4-methoxyphenyl)methoxy]-10,11-dimethyl-2-[(2S,5S)-5-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxolan-2-yl]trideca-1,6-dien-3-ol
• CAS: 1195988-08-9
• 化学式: C₆₈H₁₀₂O₉Si₃
• 分子量: 1147.81
• InChiKey: KMUPHNNBONGNGQ-YLOLKBBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.94
• 重原子数：
  80
• 可旋转键数：
  31
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3R,4R,6Z,8S,9R,10R,11S)-4,8-bis[[tert-butyl(dimethyl)silyl]oxy]-13-[tert-butyl(diphenyl)silyl]oxy-9-[(4-methoxyphenyl)methoxy]-10,11-dimethyl-2-[(2S,5S)-5-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxolan-2-yl]trideca-1,6-dien-3-ol 在 camphor-10-sulfonic acid 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.92h， 生成
  参考文献：
  名称：

  Synthetic studies on goniodomin A: convergent assembly of the C15–C36 segment via palladium-catalyzed organostannane–thioester coupling

  摘要：

  A stereocontrolled convergent synthesis of the C15-C36 segment of goniodomin A, a potent anti-angiogenic marine polyether macrolide, has been achieved using Stille-type cross-coupling reaction of a vinylstannane and a thioester as a key segment assembly process. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.017
• 作为产物：
  描述：

  C₆₈H₁₀₀O₉Si₃ 在 cerium(III) chloride heptahydrate 、 sodium tetrahydroborate 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 1.08h， 以91%的产率得到(3R,4R,6Z,8S,9R,10R,11S)-4,8-bis[[tert-butyl(dimethyl)silyl]oxy]-13-[tert-butyl(diphenyl)silyl]oxy-9-[(4-methoxyphenyl)methoxy]-10,11-dimethyl-2-[(2S,5S)-5-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxolan-2-yl]trideca-1,6-dien-3-ol
  参考文献：
  名称：

  Synthetic studies on goniodomin A: convergent assembly of the C15–C36 segment via palladium-catalyzed organostannane–thioester coupling

  摘要：

  A stereocontrolled convergent synthesis of the C15-C36 segment of goniodomin A, a potent anti-angiogenic marine polyether macrolide, has been achieved using Stille-type cross-coupling reaction of a vinylstannane and a thioester as a key segment assembly process. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.017

文献信息

• Toward the Total Synthesis of Goniodomin A, An Actin-Targeting Marine Polyether Macrolide: Convergent Synthesis of the C15−C36 Segment
  作者：Tomoyuki Saito、Haruhiko Fuwa、Makoto Sasaki

  DOI：10.1021/ol902217q

  日期：2009.11.19

  Stereoselective convergent synthesis of the C15-C36 segment of goniodomin A, an actin-targeting marine polyether macrolide natural product, has been achieved. The present synthesis features palladium(0)-catalyzed, copper(I)-mediated Liebeskind-Srogl cross-coupling as the fragment assembly process.