(4S)-4-methoxycarbonylethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 190664-56-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (4S)-4-methoxycarbonylethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-(3-methoxy-3-oxoprop-1-ynyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 190664-56-3
• 化学式: C₁₄H₂₁NO₅
• 分子量: 283.324
• InChiKey: UKDUSUZBXIBEEC-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-methoxycarbonylethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 四氧化锇 、 camphor-10-sulfonic acid 、 N-甲基吗啉氧化物 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 107.0h， 生成 (3R,4R,5R)-5-amino-3,4-dihydroxy-4-methyloxan-2-one
  参考文献：
  名称：

  Synthetic studies on maduropeptin chromophore 2. Synthesis of the madurosamine aryl amide and the C1′C9′ fragments

  摘要：

  A retrosynthetic analysis (Scheme I) of maduropeptin chromophore artifact I defined compounds 2 and 3 as required building block;. The construction of 2 was achieved starling from the 2,5-dimethyl derived aromatic acid 8 and the D-serine derived delta-lactone 12 (Scheme 2), whereas the synthesis of 3 utilized an Evans's aldol condensation reaction between aldehyde 13 and chiral auxiliary 14 (Scheme 3). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00724-7
• 作为产物：
  描述：

  氯甲酸甲酯 、 (4S)-4-乙炔基-2,2-二甲基-1,3-噁唑烷-3-甲酸叔丁酯 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以15 g的产率得到(4S)-4-methoxycarbonylethynyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis of (+)-asperazine

  摘要：

  The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is external to the ring being formed. This synthesis confirmed the structure of (+)- asperazine (1) proposed by Crews and co- workers and provided material for additional biological studies. The in vitro cytotoxicity originally reported for the marine isolate was not confirmed with synthetic (+)- asperazine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.127

文献信息

• Total synthesis of (+)-asperazine
  作者：Steven P. Govek、Larry E. Overman

  DOI：10.1016/j.tet.2007.05.127

  日期：2007.8

  The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is external to the ring being formed. This synthesis confirmed the structure of (+)- asperazine (1) proposed by Crews and co- workers and provided material for additional biological studies. The in vitro cytotoxicity originally reported for the marine isolate was not confirmed with synthetic (+)- asperazine. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthetic studies on maduropeptin chromophore 2. Synthesis of the madurosamine aryl amide and the C1′C9′ fragments
  作者：K.C. Nicolaou、Kazunori Koide、Jinyou Xu、Mark H. Izraelewicz

  DOI：10.1016/s0040-4039(97)00724-7

  日期：1997.5

  A retrosynthetic analysis (Scheme I) of maduropeptin chromophore artifact I defined compounds 2 and 3 as required building block;. The construction of 2 was achieved starling from the 2,5-dimethyl derived aromatic acid 8 and the D-serine derived delta-lactone 12 (Scheme 2), whereas the synthesis of 3 utilized an Evans's aldol condensation reaction between aldehyde 13 and chiral auxiliary 14 (Scheme 3). (C) 1997 Elsevier Science Ltd.