(S)-tert-butyl 4-((R)-1-(benzyloxy)hexadec-2-enyl)-2, 2-dimethyloxazolidine-3-carboxylate

• 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: (S)-tert-butyl 4-((R)-1-(benzyloxy)hexadec-2-enyl)-2, 2-dimethyloxazolidine-3-carboxylate
• 英文别名: tert-butyl (4S)-2,2-dimethyl-4-[(E,1R)-1-phenylmethoxyhexadec-2-enyl]-1,3-oxazolidine-3-carboxylate
• 化学式: C₃₃H₅₅NO₄
• 分子量: 529.804
• InChiKey: AXVDTCLCOHYHEQ-ARFOBUDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  38
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 4-((R)-1-(benzyloxy)hexadec-2-enyl)-2, 2-dimethyloxazolidine-3-carboxylate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 40.0h， 以77%的产率得到(E,2S,3R)-2-amino-3-phenylmethoxyoctadec-4-en-1-ol
  参考文献：
  名称：

  “Armed-disarmed” glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide

  摘要：

  A stereocontrolled synthesis of globotriaosylcernmide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting "armed-disarmed" glycosidation methodology bared on glycosyl donors and accepters carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl-(1-->4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10365-3
• 作为产物：
  描述：

  tert-butyl (S)-4-((R)-1-hydroxyallyl)-2,2-dimethyloxazolidine-3-carboxylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 8.0h， 生成 (S)-tert-butyl 4-((R)-1-(benzyloxy)hexadec-2-enyl)-2, 2-dimethyloxazolidine-3-carboxylate 、 (S)-tert-butyl 4-((R)-1-(benzyloxy)hexadec-2-enyl)-2, 2-dimethyloxazolidine-3-carboxylate
  参考文献：
  名称：

  Stereoselective total synthesis of Jaspine B (Pachastrissamine) utilizing iodocyclization and an investigation of its cytotoxic activity

  摘要：

  The stereoselective synthesis of Jaspine B has been achieved from easily available (S)-Garner's aldehyde. The trisubstituted tetrahydrofuran core of Jaspine B was constructed by utilizing a diastereoselective iodocyclization as the key step. Deiodination and debenzylation were performed in a single step by using n-Bu3SnH and ABCN as a conjugate catalyst system. The in vitro cytotoxicity of compounds 1 and la against 3 human cancer cell lines-A549 (lung), MCF7 (breast), and KB (oral): and a non-cancer cell line (NIH3T3) was determined by sulphorhodamine B based assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.07.003

文献信息

• Stereoselective total synthesis of Jaspine B (Pachastrissamine) utilizing iodocyclization and an investigation of its cytotoxic activity
  作者：Partha Ghosal、Sama Ajay、Sanjeev Meena、Sudhir Sinha、Arun K. Shaw

  DOI：10.1016/j.tetasy.2013.07.003

  日期：2013.8

  The stereoselective synthesis of Jaspine B has been achieved from easily available (S)-Garner's aldehyde. The trisubstituted tetrahydrofuran core of Jaspine B was constructed by utilizing a diastereoselective iodocyclization as the key step. Deiodination and debenzylation were performed in a single step by using n-Bu3SnH and ABCN as a conjugate catalyst system. The in vitro cytotoxicity of compounds 1 and la against 3 human cancer cell lines-A549 (lung), MCF7 (breast), and KB (oral): and a non-cancer cell line (NIH3T3) was determined by sulphorhodamine B based assay. (C) 2013 Elsevier Ltd. All rights reserved.
• “Armed-disarmed” glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide
  作者：Shun-ichi Hashimoto、Hiroki Sakamoto、Takeshi Honda、Hiroshi Abe、Sei-ichi Nakamura、Shiro Ikegami

  DOI：10.1016/s0040-4039(97)10365-3

  日期：1997.12

  A stereocontrolled synthesis of globotriaosylcernmide with three different glycosidic linkages has been accomplished by linear and convergent routes exploiting "armed-disarmed" glycosidation methodology bared on glycosyl donors and accepters carrying tetramethylphosphoroamidate as a leaving group. In particular, the convergent strategy featuring a coupling of a galactosyl-(1-->4)-galactosyl donor with a glucosylceramide derivative has proven to be extremely efficient. (C) 1997 Elsevier Science Ltd.