benzyl (2R,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate | 1226783-30-7

• 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: benzyl (2R,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate
• CAS: 1226783-30-7
• 化学式: C₂₀H₃₃NO₄Si
• 分子量: 379.572
• InChiKey: AZVYNAKNKNLFQO-NJAFHUGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (2R,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate 在 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 benzyl (2S,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-formyl-3-methylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Progress towards the Total Synthesis of Scytonemin A: Asymmetric Synthesis of (2S,3R,4R)-4-hydroxy-3-methylproline

  摘要：

  During the total synthesis of the novel cyclopeptide scytonemin A, the fragment containing two (2S,3R,4R)-4-hydroxy-3-methylproline units was successfully prepared. Two approaches leading to (2S,3R,4R)-4-hydroxy-3-methylproline have been explored. They involve the following key transformations: asymmetric crotylation, Sharpless epoxidation-subsequent epoxide opening, intramolecular amidomercuration-oxidation.

  DOI：

  10.1055/s-0029-1219208
• 作为产物：
  描述：

  benzyl N-[(2R,3R)-2-[tert-butyl(dimethyl)silyl]oxy-3-methylpent-4-enyl]carbamate 在 mercury(II) diacetate 、 sodium tetrahydroborate 、 氧气 作用下， 以 乙腈 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以26%的产率得到benzyl (2R,3R,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(hydroxymethyl)-3-methylpyrrolidine-1-carboxylate
  参考文献：
  名称：

  Progress towards the Total Synthesis of Scytonemin A: Asymmetric Synthesis of (2S,3R,4R)-4-hydroxy-3-methylproline

  摘要：

  During the total synthesis of the novel cyclopeptide scytonemin A, the fragment containing two (2S,3R,4R)-4-hydroxy-3-methylproline units was successfully prepared. Two approaches leading to (2S,3R,4R)-4-hydroxy-3-methylproline have been explored. They involve the following key transformations: asymmetric crotylation, Sharpless epoxidation-subsequent epoxide opening, intramolecular amidomercuration-oxidation.

  DOI：

  10.1055/s-0029-1219208

文献信息

• Progress towards the Total Synthesis of Scytonemin A: Asymmetric Synthesis of (2S,3R,4R)-4-hydroxy-3-methylproline
  作者：Zhengshuang Xu、Tao Ye、Lei Wang、Junyang Liu、Hui Zhang

  DOI：10.1055/s-0029-1219208

  日期：2010.3

  During the total synthesis of the novel cyclopeptide scytonemin A, the fragment containing two (2S,3R,4R)-4-hydroxy-3-methylproline units was successfully prepared. Two approaches leading to (2S,3R,4R)-4-hydroxy-3-methylproline have been explored. They involve the following key transformations: asymmetric crotylation, Sharpless epoxidation-subsequent epoxide opening, intramolecular amidomercuration-oxidation.