((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 | 1039740-36-7

• 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)-1-(benzyloxy)-3-(2,2-dimethoxyethyl)-2-((4-methoxybenzyloxy)methyl)-3-methyl-7-oxabicyclo[4.2.0]octan-4-yloxy)(tert-butyl)dimethylsilane
• 英文别名: tert-butyl-[[(1S,2R,3S,4S,6R)-3-(2,2-dimethoxyethyl)-2-[(4-methoxyphenyl)methoxymethyl]-3-methyl-1-phenylmethoxy-7-oxabicyclo[4.2.0]octan-4-yl]oxy]-dimethylsilane
• CAS: 1039740-36-7
• 化学式: C₃₄H₅₂O₇Si
• 分子量: 600.868
• InChiKey: IQIJTXGTKUMQKU-VTHVVLAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((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 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以95%的产率得到((1S,2R,3S,4S,6R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-(2,2-dimethoxyethyl)-3-methyl-7-oxabicyclo[4.2.0]octan-2-yl)methanol
  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,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

文献信息

• Highly Efficient Stereocontrolled Synthesis of Danishefsky’s Taxol CD Ring Key Intermediate
  作者：Paul Brémond、Gérard Audran、Honoré Monti

  DOI：10.1021/jo800913x

  日期：2008.8.1

  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.