4-Methyl-2-(3-methyl-thioureido)-pent-4-enoic acid tert-butyl ester | 785803-37-4

• 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: 4-Methyl-2-(3-methyl-thioureido)-pent-4-enoic acid tert-butyl ester
• 英文别名: Tert-butyl 4-methyl-2-(methylcarbamothioylamino)pent-4-enoate
• CAS: 785803-37-4
• 化学式: C₁₂H₂₂N₂O₂S
• 分子量: 258.385
• InChiKey: FUPDNWLGWOMWSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methyl-2-(3-methyl-thioureido)-pent-4-enoic acid tert-butyl ester 在 盐酸 、 硫化氢 、 silver trifluoroacetate 、 一溴化碘 、 三乙胺 、 尿素 作用下， 以 吡啶 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 (4S,6S)-6-Hydroxymethyl-1,6-dimethyl-1,4,5,6-tetrahydro-pyrimidine-4-carboxylic acid
  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：

  甘氨酸叔丁酯盐酸盐 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 4-Methyl-2-(3-methyl-thioureido)-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

• 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.