tert-butyl (2R,4S,5R)-5-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3-carboxylate | 155396-68-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tert-butyl (2R,4S,5R)-5-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3-carboxylate
• 英文别名: tert-butyl (2R,4S,5R)-5-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3-carboxylate
• CAS: 155396-68-2
• 化学式: C₃₂H₄₀N₂O₇S
• 分子量: 596.745
• InChiKey: OIPWHACIELMRSJ-MDDBUKAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,4S,5R)-5-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3-carboxylate 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 以100%的产率得到(2R、4S、5R)-2-(4-甲氧基苯基)-4-苯基-3、5-恶唑烷二羧酸 3-叔丁酯
  参考文献：
  名称：

  Highly Stereocontrolled and Efficient Preparation of the Protected, Esterification-Ready Docetaxel (Taxotere) Side Chain

  摘要：

  A high-yield synthesis of the p-methoxybenzylidene-protected docetaxel (Taxotere) side chain, a useful derivative for efficient, epimerization-free esterification of the 7,10-bis[(trichloroethoxy)carbonyl] derivative of 10-desacetylbaccatin III for the preparation of docetaxel, has been effected; the C-4 and C-5 stereocenters of the 1,3-oxazolidine are generated with complete (greater-than-or-equal-to 99%) stereocontrol whereas that at C-2 is produced with 96% selectivity.

  DOI：

  10.1021/jo00085a004
• 作为产物：
  描述：

  benzaldehyde N-boc imine 在 4 A molecular sieve 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 14.75h， 生成 tert-butyl (2R,4S,5R)-5-[(1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Highly Stereocontrolled and Efficient Preparation of the Protected, Esterification-Ready Docetaxel (Taxotere) Side Chain

  摘要：

  A high-yield synthesis of the p-methoxybenzylidene-protected docetaxel (Taxotere) side chain, a useful derivative for efficient, epimerization-free esterification of the 7,10-bis[(trichloroethoxy)carbonyl] derivative of 10-desacetylbaccatin III for the preparation of docetaxel, has been effected; the C-4 and C-5 stereocenters of the 1,3-oxazolidine are generated with complete (greater-than-or-equal-to 99%) stereocontrol whereas that at C-2 is produced with 96% selectivity.

  DOI：

  10.1021/jo00085a004

文献信息

• Highly Stereocontrolled and Efficient Preparation of the Protected, Esterification-Ready Docetaxel (Taxotere) Side Chain
  作者：Alice M. Kanazawa、Jean-Noel Denis、Andrew E. Greene

  DOI：10.1021/jo00085a004

  日期：1994.3

  A high-yield synthesis of the p-methoxybenzylidene-protected docetaxel (Taxotere) side chain, a useful derivative for efficient, epimerization-free esterification of the 7,10-bis[(trichloroethoxy)carbonyl] derivative of 10-desacetylbaccatin III for the preparation of docetaxel, has been effected; the C-4 and C-5 stereocenters of the 1,3-oxazolidine are generated with complete (greater-than-or-equal-to 99%) stereocontrol whereas that at C-2 is produced with 96% selectivity.