(1S,5S)-1-[(2S,3S)-3-[(E,2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(4-methoxyphenyl)methoxy]-5-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]pent-4-enyl]oxiran-2-yl]-6-[(2R,6R)-6-[4-[(4-methoxyphenyl)methoxy]but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl]-5-methyl-3-methylidenehexan-1-ol | 464914-21-4

• 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: (1S,5S)-1-[(2S,3S)-3-[(E,2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(4-methoxyphenyl)methoxy]-5-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]pent-4-enyl]oxiran-2-yl]-6-[(2R,6R)-6-[4-[(4-methoxyphenyl)methoxy]but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl]-5-methyl-3-methylidenehexan-1-ol
• CAS: 464914-21-4
• 化学式: C₅₂H₇₄O₉Si
• 分子量: 871.24
• InChiKey: VQQCUHZDBUZMDY-CCUHOOIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.48
• 重原子数：
  62
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  97.4
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S,5S)-1-[(2S,3S)-3-[(E,2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(4-methoxyphenyl)methoxy]-5-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]pent-4-enyl]oxiran-2-yl]-6-[(2R,6R)-6-[4-[(4-methoxyphenyl)methoxy]but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl]-5-methyl-3-methylidenehexan-1-ol 在 Lindlar's catalyst 喹啉 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 1-己烯 、 2,4,6-三氯苯甲酰氯 、 氢气 、 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 、 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 6.0h， 生成 (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 sodium tetrahydroborate 、 cerium(III) chloride 、 三氟化硼乙醚 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (1S,5S)-1-[(2S,3S)-3-[(E,2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(4-methoxyphenyl)methoxy]-5-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]pent-4-enyl]oxiran-2-yl]-6-[(2R,6R)-6-[4-[(4-methoxyphenyl)methoxy]but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl]-5-methyl-3-methylidenehexan-1-ol
  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.