(1R,3S,7S,8R,10S,12S,18R)-7-(tert-Butyl-dimethyl-silanyloxy)-12-[(E)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docos-19-en-15-yn-14-one | 464914-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (1R,3S,7S,8R,10S,12S,18R)-7-(tert-Butyl-dimethyl-silanyloxy)-12-[(E)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docos-19-en-15-yn-14-one
• 英文别名: (1R,3S,7S,8R,10S,12S,18R)-7-[tert-butyl(dimethyl)silyl]oxy-12-[(E,1S)-1-[tert-butyl(dimethyl)silyl]oxy-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]prop-2-enyl]-3-methyl-5-methylidene-9,13,22-trioxatricyclo[16.3.1.08,10]docos-19-en-15-yn-14-one
• CAS: 464914-11-2
• 化学式: C₄₂H₆₈O₇Si₂
• 分子量: 741.169
• InChiKey: HMBFBSWNNRDDJW-ZVUKAOEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.61
• 重原子数：
  51
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R,3S,7S,8R,10S,12S,18R)-7-(tert-Butyl-dimethyl-silanyloxy)-12-[(E)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docos-19-en-15-yn-14-one 在 Lindlar's catalyst 喹啉 、 1-己烯 、 氢气 作用下， 以 丙酮 为溶剂， 以95%的产率得到(1R,3S,7S,8R,10S,12S,15Z,18R)-7-[tert-butyl(dimethyl)silyl]oxy-12-[(E,1S)-1-[tert-butyl(dimethyl)silyl]oxy-3-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]prop-2-enyl]-3-methyl-5-methylidene-9,13,22-trioxatricyclo[16.3.1.08,10]docosa-15,19-dien-14-one
  参考文献：
  名称：

  Synthesis of (−)-laulimalide: an agent for microtubule stabilization

  摘要：

  An enantioselective synthesis or (-)-laulimalide is described. Key reactions include a convergent allylation coupling reaction, asymmetric conjugate addition, the allenylstannane Ferrier reaction and a chelation-controlled alkenylzine addition as the basis for stereocontrol in critical elements of chirality. (C) 20021 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00907-3
• 作为产物：
  描述：

  methyl (3R)-3-methyl-5-oxopentanoate 在 R,R-Jacobsen's catalyst 4-二甲氨基吡啶 、 manganese(IV) oxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 2,4,6-三氯苯甲酰氯 、 三氟化硼乙醚 、 三乙胺 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 13.0h， 生成 (1R,3S,7S,8R,10S,12S,18R)-7-(tert-Butyl-dimethyl-silanyloxy)-12-[(E)-(S)-1-(tert-butyl-dimethyl-silanyloxy)-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-3-methyl-5-methylene-9,13,22-trioxa-tricyclo[16.3.1.0^8,10]docos-19-en-15-yn-14-one
  参考文献：
  名称：

  Synthesis of (−)-laulimalide: an agent for microtubule stabilization

  摘要：

  An enantioselective synthesis or (-)-laulimalide is described. Key reactions include a convergent allylation coupling reaction, asymmetric conjugate addition, the allenylstannane Ferrier reaction and a chelation-controlled alkenylzine addition as the basis for stereocontrol in critical elements of chirality. (C) 20021 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00907-3

文献信息

• Synthesis of (−)-laulimalide: an agent for microtubule stabilization
  作者：David R. Williams、Liang Mi、Richard J. Mullins、Ryan E. Stites

  DOI：10.1016/s0040-4039(02)00907-3

  日期：2002.7

  An enantioselective synthesis or (-)-laulimalide is described. Key reactions include a convergent allylation coupling reaction, asymmetric conjugate addition, the allenylstannane Ferrier reaction and a chelation-controlled alkenylzine addition as the basis for stereocontrol in critical elements of chirality. (C) 20021 Elsevier Science Ltd. All rights reserved.