[3-[[(2R,3S)-3,4-dihydroxy-1-phenylsulfanylbutan-2-yl]carbamoyl]-2-methylphenyl] acetate | 767341-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: [3-[[(2R,3S)-3,4-dihydroxy-1-phenylsulfanylbutan-2-yl]carbamoyl]-2-methylphenyl] acetate
• CAS: 767341-27-5
• 化学式: C₂₀H₂₃NO₅S
• 分子量: 389.472
• InChiKey: XOHXSQSJKZAVIR-ZWKOTPCHSA-N

物化性质

• 沸点：
  612.3±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-叔丁基-十氢异喹啉-3(S)-甲酰胺 、 [3-[[(2R,3S)-3,4-dihydroxy-1-phenylsulfanylbutan-2-yl]carbamoyl]-2-methylphenyl] acetate 在 三乙胺 、 对甲苯磺酰氯 作用下， 以59%的产率得到奈非那韦
  参考文献：
  名称：

  A short synthesis of the HIV-protease inhibitor nelfinavir via a diastereoselective addition of ammonia to the α,β-unsaturated sulfoxide derived from ( R )-glyceraldehyde acetonide

  摘要：

  Diastereoselective Michael addition of ammonia to sulfoxide 3a derived from (R)-glyceraldehyde acetonide provides amine 4a, which is converted into Nelfinavir using (BF3Et2O)-Et-./Nal reduction and subsequent coupling reactions as key steps. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02077-4
• 作为产物：
  描述：

  [3-[[(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-phenylsulfanylethyl]carbamoyl]-2-methylphenyl] acetate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到[3-[[(2R,3S)-3,4-dihydroxy-1-phenylsulfanylbutan-2-yl]carbamoyl]-2-methylphenyl] acetate
  参考文献：
  名称：

  A short synthesis of the HIV-protease inhibitor nelfinavir via a diastereoselective addition of ammonia to the α,β-unsaturated sulfoxide derived from ( R )-glyceraldehyde acetonide

  摘要：

  Diastereoselective Michael addition of ammonia to sulfoxide 3a derived from (R)-glyceraldehyde acetonide provides amine 4a, which is converted into Nelfinavir using (BF3Et2O)-Et-./Nal reduction and subsequent coupling reactions as key steps. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02077-4

文献信息

• Tetrahedron Lett. 2002, 43, 8511-8513
  作者：

  DOI：——

  日期：——
• A short synthesis of the HIV-protease inhibitor nelfinavir via a diastereoselective addition of ammonia to the α,β-unsaturated sulfoxide derived from ( R )-glyceraldehyde acetonide
  作者：Dawei Ma、Bin Zou、Wei Zhu、Huadong Xu

  DOI：10.1016/s0040-4039(02)02077-4

  日期：2002.11

  Diastereoselective Michael addition of ammonia to sulfoxide 3a derived from (R)-glyceraldehyde acetonide provides amine 4a, which is converted into Nelfinavir using (BF3Et2O)-Et-./Nal reduction and subsequent coupling reactions as key steps. (C) 2002 Elsevier Science Ltd. All rights reserved.