2-(2,3-Dimethyl-isothioureido)-4-methyl-pent-4-enoic acid tert-butyl ester | 550346-65-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2,3-Dimethyl-isothioureido)-4-methyl-pent-4-enoic acid tert-butyl ester
• 英文别名: tert-butyl 4-methyl-2-[[methylamino(methylsulfanyl)methylidene]amino]pent-4-enoate
• CAS: 550346-65-1
• 化学式: C₁₃H₂₄N₂O₂S
• 分子量: 272.412
• InChiKey: FINPSAHEQFJWOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  76
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,3-Dimethyl-isothioureido)-4-methyl-pent-4-enoic acid tert-butyl ester 在 一溴化碘 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到(4R,6S)-6-Iodomethyl-1,6-dimethyl-2-methylsulfanyl-1,4,5,6-tetrahydro-pyrimidine-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis of (±)-manzacidin D

  摘要：

  We report herein the first total synthesis of the alkaloid manzacidin D, in 11 steps and 16% overall yield from commercially available glycine tert-butyl ester hydrochloride. Our synthesis demonstrates for the first time in a total synthesis the utility of two different methodologies. A highly diastereoselective iodocyclization of an olefinic isothiourea is used to induce stereocontrol at the quaternary centre, and to form the heterocyclic core. Conversion of a thiourea to the requisite formamidine is achieved in good yield using our modified procedure. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.038
• 作为产物：
  描述：

  tert-butyl 2-amino-4-methylpent-4-enoate 以 吡啶 、 乙腈 为溶剂， 生成 2-(2,3-Dimethyl-isothioureido)-4-methyl-pent-4-enoic acid tert-butyl ester
  参考文献：
  名称：

  Total synthesis of (±)-manzacidin D

  摘要：

  We report herein the first total synthesis of the alkaloid manzacidin D, in 11 steps and 16% overall yield from commercially available glycine tert-butyl ester hydrochloride. Our synthesis demonstrates for the first time in a total synthesis the utility of two different methodologies. A highly diastereoselective iodocyclization of an olefinic isothiourea is used to induce stereocontrol at the quaternary centre, and to form the heterocyclic core. Conversion of a thiourea to the requisite formamidine is achieved in good yield using our modified procedure. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.038

文献信息

• Diastereoselective isothiourea iodocyclization for manzacidin synthesis
  作者：Jacqueline C.S. Woo、D.Bruce MacKay

  DOI：10.1016/s0040-4039(03)00431-3

  日期：2003.3

  We have devised a novel strategy for the total synthesis of the manzacidins. Our approach utilizes an isothiourea iodocyclization strategy to directly form the heterocyclic core, and in the process induce stereoselectivity at the quaternary center. We have found that cyclization can be achieved using an isothiourea as the nucleophilic partner. Cyclization proceeds smoothly using IBr at low temperature

  我们已经设计了一种新颖的策略，用于全合成山梨酸。我们的方法利用异硫脲的碘环化策略直接形成杂环核心，并在此过程中在四元中心诱导立体选择性。我们发现使用异硫脲作为亲核伴侣可以实现环化。在低温下使用IBr可以顺利进行环化反应，从而以我们拟议的路线提供了先进的中间体，以92％的收率获得了甘露糖苷A。我们已经通过制备几种环状异硫脲证明了反应的范围，其中包括我们拟议的路线中合成甘露酸D的中间体。
• Total synthesis of (±)-manzacidin D
  作者：Christian Drouin、Jacqueline C.S. Woo、D. Bruce MacKay、Roch M.A. Lavigne

  DOI：10.1016/j.tetlet.2004.08.038

  日期：2004.9

  We report herein the first total synthesis of the alkaloid manzacidin D, in 11 steps and 16% overall yield from commercially available glycine tert-butyl ester hydrochloride. Our synthesis demonstrates for the first time in a total synthesis the utility of two different methodologies. A highly diastereoselective iodocyclization of an olefinic isothiourea is used to induce stereocontrol at the quaternary centre, and to form the heterocyclic core. Conversion of a thiourea to the requisite formamidine is achieved in good yield using our modified procedure. (C) 2004 Elsevier Ltd. All rights reserved.