trimethyl-[1-[(2S,5S)-5-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxolan-2-yl]ethenyl]stannane | 1195988-10-3

• 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: trimethyl-[1-[(2S,5S)-5-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxolan-2-yl]ethenyl]stannane
• CAS: 1195988-10-3
• 化学式: C₂₂H₃₂O₃Sn
• 分子量: 463.204
• InChiKey: GWYKXUJYODNIKG-RQRFPZIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

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-(p-tolyl) (R,Z)-6-((tert-butyldimethylsilyl)oxy)-2-((triisopropylsilyl)oxy)hex-4-enethioate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 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， 以60%的产率得到(R,Z)-2-((2S,5S)-5-((2R,6S)-6-((benzyloxy)methyl)-5,6-dihydro-2H-pyran-2-yl)tetrahydrofuran-2-yl)-8-((tert-butyldimethylsilyl)oxy)-4-((triisopropylsilyl)oxy)octa-1,6-dien-3-one
  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：

  1-((2S,5S)-5-((2R,6S)-6-((benzyloxy)methyl)-5,6-dihydro-2H-pyran-2-yl)tetrahydrofuran-2-yl)vinyl trifluoromethanesulfonate 、 六甲基二锡 在 四(三苯基膦)钯 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到trimethyl-[1-[(2S,5S)-5-[(2S,6R)-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxolan-2-yl]ethenyl]stannane
  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

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.