(1S,2R,3S,4S,6R)-4-(tert-butyldimethylsilyloxy)-3-(2,2-dimethoxyethyl)-2-((4-methoxybenzyloxy)methyl)-3-methyl-7-oxabicyclo[4.2.0]octan-1-ol | 1039740-34-5

• 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,2R,3S,4S,6R)-4-(tert-butyldimethylsilyloxy)-3-(2,2-dimethoxyethyl)-2-((4-methoxybenzyloxy)methyl)-3-methyl-7-oxabicyclo[4.2.0]octan-1-ol
• 英文别名: (1S,2R,3S,4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-3-(2,2-dimethoxyethyl)-2-[(4-methoxyphenyl)methoxymethyl]-3-methyl-7-oxabicyclo[4.2.0]octan-1-ol
• CAS: 1039740-34-5
• 化学式: C₂₇H₄₆O₇Si
• 分子量: 510.744
• InChiKey: CYUYUUPSFNSGMZ-VPZBFSRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4S,6R)-4-(tert-butyldimethylsilyloxy)-3-(2,2-dimethoxyethyl)-2-((4-methoxybenzyloxy)methyl)-3-methyl-7-oxabicyclo[4.2.0]octan-1-ol 、 溴甲苯 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以87%的产率得到((1S,2R,3S,4S,6R)-1-(benzyloxy)-3-(2,2-dimethoxyethyl)-2-((4-methoxybenzyloxy)methyl)-3-methyl-7-oxabicyclo[4.2.0]octan-4-yloxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Highly Efficient Stereocontrolled Synthesis of Danishefsky’s Taxol CD Ring Key Intermediate

  摘要：

  Danishefsky's taxol CD ring key intermediate is synthesized in 15 steps and 11.4% overall yield from a readily available starting material. Absolute stereochemistry of the starting material and stereocontrolled steps determine the absolute configuration of the five requisite contiguous stereocenters.

  DOI：

  10.1021/jo800913x
• 作为产物：
  描述：

  [(1S,2S,3R,4S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-4-(2,2-dimethoxyethyl)-2-hydroxy-2-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxymethyl]-4-methylcyclohexyl] methanesulfonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以125 mg的产率得到(1S,2R,3S,4S,6R)-4-(tert-butyldimethylsilyloxy)-3-(2,2-dimethoxyethyl)-2-((4-methoxybenzyloxy)methyl)-3-methyl-7-oxabicyclo[4.2.0]octan-1-ol
  参考文献：
  名称：

  Highly Efficient Stereocontrolled Synthesis of Danishefsky’s Taxol CD Ring Key Intermediate

  摘要：

  Danishefsky's taxol CD ring key intermediate is synthesized in 15 steps and 11.4% overall yield from a readily available starting material. Absolute stereochemistry of the starting material and stereocontrolled steps determine the absolute configuration of the five requisite contiguous stereocenters.

  DOI：

  10.1021/jo800913x