tert-Butyl-[(Z)-4-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyloxy]-dimethyl-silane | 911834-82-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-[(Z)-4-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyloxy]-dimethyl-silane
• 英文别名: tert-butyl-[(Z)-4-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]but-3-enoxy]-dimethylsilane
• CAS: 911834-82-7
• 化学式: C₁₇H₃₂O₃Si
• 分子量: 312.525
• InChiKey: KEGGKCVELLAKER-OJBGHLBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  tert-Butyl-[(Z)-4-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyloxy]-dimethyl-silane 在 盐酸 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 D-tartaric acid derivative 、 四丁基氟化铵 、 potassium carbonate 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 异丙醇 为溶剂， 反应 137.21h， 生成 4-[(2R,6R)-6-((E)-(2S,6S,10S,11S)-10,11-Dihydroxy-6-methoxymethoxy-2-methyl-4-methylene-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-ynoic acid
  参考文献：
  名称：

  Pharmacophore Mapping in the Laulimalide Series:  Total Synthesis of a Vinylogue for a Late-Stage Metathesis Diversification Strategy

  摘要：

  An efficient synthesis of the macrocyclic core of laulimalide with a pendant vinyl group at C20 is described, allowing for late-stage introduction of various side chains through a selective and efficient cross metathesis diversification step. Representative analogues reported herein are the first to contain modifications to only the side chain dihydropyran of laulimalide and des-epoxy laulimalide. This step-economical strategy enables the rapid synthesis of new analogues using alkenes as an inexpensive, abundantly available diversification feedstock.

  DOI：

  10.1021/ol061619u
• 作为产物：
  描述：

  ((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)methanol 在 草酰氯 、 sodium hexamethyldisilazane 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.67h， 生成 tert-Butyl-[(Z)-4-((4S,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyloxy]-dimethyl-silane
  参考文献：
  名称：

  Pharmacophore Mapping in the Laulimalide Series:  Total Synthesis of a Vinylogue for a Late-Stage Metathesis Diversification Strategy

  摘要：

  An efficient synthesis of the macrocyclic core of laulimalide with a pendant vinyl group at C20 is described, allowing for late-stage introduction of various side chains through a selective and efficient cross metathesis diversification step. Representative analogues reported herein are the first to contain modifications to only the side chain dihydropyran of laulimalide and des-epoxy laulimalide. This step-economical strategy enables the rapid synthesis of new analogues using alkenes as an inexpensive, abundantly available diversification feedstock.

  DOI：

  10.1021/ol061619u

文献信息

• Pharmacophore Mapping in the Laulimalide Series:  Total Synthesis of a Vinylogue for a Late-Stage Metathesis Diversification Strategy
  作者：Paul A. Wender、Michael K. Hilinski、Philip R. Skaanderup、Nicolas G. Soldermann、Susan L. Mooberry

  DOI：10.1021/ol061619u

  日期：2006.8.1

  An efficient synthesis of the macrocyclic core of laulimalide with a pendant vinyl group at C20 is described, allowing for late-stage introduction of various side chains through a selective and efficient cross metathesis diversification step. Representative analogues reported herein are the first to contain modifications to only the side chain dihydropyran of laulimalide and des-epoxy laulimalide. This step-economical strategy enables the rapid synthesis of new analogues using alkenes as an inexpensive, abundantly available diversification feedstock.