2-(2-benzyloxy-ethyl)-6-[2,3,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-methyl-oct-7-enyl]-tetrahydro-pyran | 1012319-36-6

• 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: 2-(2-benzyloxy-ethyl)-6-[2,3,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-methyl-oct-7-enyl]-tetrahydro-pyran
• 英文别名: [(2R,4S,6R,7S)-2,6-bis[[tert-butyl(dimethyl)silyl]oxy]-7-methyl-1-[(2S,6R)-6-(2-phenylmethoxyethyl)oxan-2-yl]non-8-en-4-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1012319-36-6
• 化学式: C₄₂H₈₀O₅Si₃
• 分子量: 749.351
• InChiKey: LGCRADSMFAOKJY-BLCAPVSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.69
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6,7-tris(tert-butyl-dimethyl-silanyloxy)-4-methoxy-heptanoic acid methyl ester 、 2-(2-benzyloxy-ethyl)-6-[2,3,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-methyl-oct-7-enyl]-tetrahydro-pyran 在 titanium(IV)isopropoxide 、 环己基溴化镁 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到2-[7-[6-(2-benzyloxy-ethyl)-tetrahydro-pyran-2-yl]-2,4,6-tris-(tert-butyl-dimethyl-silanyloxy)-1-methyl-heptyl]-1-[4,5,6-tris-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-hexyl]-cyclopropanol
  参考文献：
  名称：

  Toward the Synthesis of Spirastrellolide B:  A Synthesis of the C1−C23 Subunit

  摘要：

  A synthesis of the C1-C23 subunit of spirastrellolide B is described. The synthesis features two applications of a Kulinkovich-cyclopropanol ring-opening strategy for the coupling of esters with olefins to produce ketones.

  DOI：

  10.1021/ol702955m
• 作为产物：
  描述：

  1-[6-(2-benzyloxy-ethyl)-tetrahydro-pyran-2-yl]-5-(tert-butyl-dimethyl-silanyloxy)-6-methyl-oct-7-en-2,3-diol 、 叔丁基二甲硅基三氟甲磺酸酯 在 三乙胺 作用下， 以 dichlomethane 为溶剂， 反应 1.0h， 以82%的产率得到2-(2-benzyloxy-ethyl)-6-[2,3,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-methyl-oct-7-enyl]-tetrahydro-pyran
  参考文献：
  名称：

  Toward the Synthesis of Spirastrellolide B:  A Synthesis of the C1−C23 Subunit

  摘要：

  A synthesis of the C1-C23 subunit of spirastrellolide B is described. The synthesis features two applications of a Kulinkovich-cyclopropanol ring-opening strategy for the coupling of esters with olefins to produce ketones.

  DOI：

  10.1021/ol702955m

文献信息

• Toward the Synthesis of Spirastrellolide B:  A Synthesis of the C1−C23 Subunit
  作者：Katie A. Keaton、Andrew J. Phillips

  DOI：10.1021/ol702955m

  日期：2008.3.1

  A synthesis of the C1-C23 subunit of spirastrellolide B is described. The synthesis features two applications of a Kulinkovich-cyclopropanol ring-opening strategy for the coupling of esters with olefins to produce ketones.