(2RS,1'S)-2-<1'-((tert-butoxycarbonyl)amino)-2'-phenylethyl>-1,3-thiazolidine | 120205-64-3

• 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: (2RS,1'S)-2-<1'-((tert-butoxycarbonyl)amino)-2'-phenylethyl>-1,3-thiazolidine
• 英文别名: N-(tert-butoxycarbonyl)-S-tetrahydrodolaphenine；(2RS,1'S)-2-{1'-[(tert-butoxycarbonyl)amino]-2'-phenylethyl}-1,3-thiazolidine；tert-butyl N-[(1S)-2-phenyl-1-(1,3-thiazolidin-2-yl)ethyl]carbamate
• CAS: 120205-64-3；120205-65-4；133164-09-7；133164-10-0；144775-23-5
• 化学式: C₁₆H₂₄N₂O₂S
• 分子量: 308.445
• InChiKey: WDRQIFVROXDUQW-LSLKUGRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  75.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2RS,1'S)-2-<1'-((tert-butoxycarbonyl)amino)-2'-phenylethyl>-1,3-thiazolidine 在 盐酸 、 manganese(IV) oxide 、 氢溴酸 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 溶剂黄146 、 三乙胺 、 焦碳酸二乙酯 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 202.33h， 生成 (S)-2-((S)-2-(二甲基氨基)-3-甲基丁酰氨基)-N-((3R,4S,5S)-3-甲氧基-1-((s)-2-((1R,2R)-1-甲氧基-2-甲基-3-氧代-3-(((S)-2-苯基-1-(噻唑-2-基）乙基)氨基)丙基)吡咯烷-1-基)-5-甲基-1-氧代庚烷-4-基)-N,3-二甲基丁酰胺
  参考文献：
  名称：

  An expeditious synthesis of dolastatin 10

  摘要：

  Total synthesis of dolastatin 10 (1) was completed by developing an efficient synthesis of two key amino acid components, Dil (6) and Dap (11), and subsequent stepwise coupling of five amino acid components from C-terminal Doe.

  DOI：

  10.1016/s0040-4039(00)79932-1
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醇 在 pyridine-SO3 complex 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 18.67h， 生成 (2RS,1'S)-2-<1'-((tert-butoxycarbonyl)amino)-2'-phenylethyl>-1,3-thiazolidine
  参考文献：
  名称：

  A new efficient synthesis of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine), the C-terminal unit of dolastatin 10

  摘要：

  Four methods for the preparation of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine, 2), which constitutes the C-terminal unit of dolastatin 10 (1) having strong anticancer activity, has been investigated. Of these, the most efficient one involved the acylation of 2-lithiothiazole with N-methoxy-N-methylphenylacetamide (8), asymmetric reduction with (+)-diisopinocampheylchloroborane (11g), followed by the modified Mitsunobu reaction utilizing diphenyl phosphorazidate.

  DOI：

  10.1016/s0040-4020(01)88264-8

文献信息

• Pettit, George R.; Hogan, Fiona; Burkett, Douglas D., Heterocycles, 1994, vol. 39, # 1, p. 81 - 100
  作者：Pettit, George R.、Hogan, Fiona、Burkett, Douglas D.、Singh, Sheo B.、Kentoci, Darko、et al.

  DOI：——

  日期：——
• An expeditious synthesis of dolastatin 10
  作者：Kiyoshi Tomioka、Motomu Kanai、Kenji Koga

  DOI：10.1016/s0040-4039(00)79932-1

  日期：1991.5

  Total synthesis of dolastatin 10 (1) was completed by developing an efficient synthesis of two key amino acid components, Dil (6) and Dap (11), and subsequent stepwise coupling of five amino acid components from C-terminal Doe.
• A new efficient synthesis of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine), the C-terminal unit of dolastatin 10
  作者：Naoko Irako、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4020(01)88264-8

  日期：1992.1

  Four methods for the preparation of (S)-dolaphenine ((S)-2-phenyl-1-(2-thiazolyl)ethylamine, 2), which constitutes the C-terminal unit of dolastatin 10 (1) having strong anticancer activity, has been investigated. Of these, the most efficient one involved the acylation of 2-lithiothiazole with N-methoxy-N-methylphenylacetamide (8), asymmetric reduction with (+)-diisopinocampheylchloroborane (11g), followed by the modified Mitsunobu reaction utilizing diphenyl phosphorazidate.