S-(4-methylphenyl) (Z,2R,6S,7R,8R,9S)-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-11-[tert-butyl(diphenyl)silyl]oxy-7-[(4-methoxyphenyl)methoxy]-8,9-dimethylundec-4-enethioate | 1195988-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: S-(4-methylphenyl) (Z,2R,6S,7R,8R,9S)-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-11-[tert-butyl(diphenyl)silyl]oxy-7-[(4-methoxyphenyl)methoxy]-8,9-dimethylundec-4-enethioate
• CAS: 1195988-11-4
• 化学式: C₅₆H₈₄O₆SSi₃
• 分子量: 969.602
• InChiKey: SXBBUCGOVFBIQF-JDXQKGFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.17
• 重原子数：
  66
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trimethyl-[1-[(2S,5S)-5-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxolan-2-yl]ethenyl]stannane 、 S-(4-methylphenyl) (Z,2R,6S,7R,8R,9S)-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-11-[tert-butyl(diphenyl)silyl]oxy-7-[(4-methoxyphenyl)methoxy]-8,9-dimethylundec-4-enethioate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 二苯基磷酸亚铜 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以68%的产率得到C₆₈H₁₀₀O₉Si₃
  参考文献：
  名称：

  Toward the Total Synthesis of Goniodomin A, An Actin-Targeting Marine Polyether Macrolide: Convergent Synthesis of the C15−C36 Segment

  摘要：

  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.

  DOI：

  10.1021/ol902217q
• 作为产物：
  描述：

  (2R,6S,7R,8R,9S,Z)-11-((tert-butyldiphenylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-8,9-dimethyl-1-(trityloxy)undec-4-ene-2,6-diol 在 2,6-二甲基吡啶 、 甲醇 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 zinc dibromide 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 20.33h， 生成 S-(4-methylphenyl) (Z,2R,6S,7R,8R,9S)-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-11-[tert-butyl(diphenyl)silyl]oxy-7-[(4-methoxyphenyl)methoxy]-8,9-dimethylundec-4-enethioate
  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

• Synthetic studies on goniodomin A: convergent assembly of the C15–C36 segment via palladium-catalyzed organostannane–thioester coupling
  作者：Tomoyuki Saito、Haruhiko Fuwa、Makoto Sasaki

  DOI：10.1016/j.tet.2010.11.017

  日期：2011.1

  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.
• 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.