[(2S)-3-methyl-2-[(4-methylphenyl)sulfonylamino]butyl] propanoate | 479483-89-1

• 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: [(2S)-3-methyl-2-[(4-methylphenyl)sulfonylamino]butyl] propanoate
• CAS: 479483-89-1
• 化学式: C₁₅H₂₃NO₄S
• 分子量: 313.418
• InChiKey: OMELPXHMQQXSTN-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苄氧基乙醛 、 [(2S)-3-methyl-2-[(4-methylphenyl)sulfonylamino]butyl] propanoate 在 四氯化钛 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [(2S)-3-methyl-2-[(4-methylphenyl)sulfonylamino]butyl] (2S,3S)-3-hydroxy-2-methyl-4-phenylmethoxybutanoate
  参考文献：
  名称：

  Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes

  摘要：

  A chelation-controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of (S)-valinolderived ester with a variety of aldehydes proceeded with high syn-diastercoselectivities (up to 99:1) and isolated yields (94%). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01113-9
• 作为产物：
  描述：

  L-缬氨醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 [(2S)-3-methyl-2-[(4-methylphenyl)sulfonylamino]butyl] propanoate
  参考文献：
  名称：

  Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes

  摘要：

  A chelation-controlled and highly diastereoselective synthesis of syn-aldols is described. Aldol reaction of (S)-valinolderived ester with a variety of aldehydes proceeded with high syn-diastercoselectivities (up to 99:1) and isolated yields (94%). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01113-9

文献信息

• Highly diastereoselective asymmetric syn-aldol reactions of (R)-(N-tosyl)phenylalaninol propionate-derived titanium enolate and bidentate aromatic and aliphatic aldehydes
  作者：Arun K. Ghosh、John P. Gulliver

  DOI：10.1016/j.tetlet.2022.153954

  日期：2022.7

  aromatic aldehydes to provide syn-aldol products with high diastereoselectivity and isolated yields. Both enantiomers of N-(tosyl)phenylalaninol are readily prepared from commercially available and optically active phenylalaninol. Mild saponification removed the chiral auxiliary and furnished optically active β-hydroxy carboxylic acids.

  已经研究了( R )-( N-甲苯磺酰基)苯丙氨醇丙酸酯和二齿芳香醛的酯衍生钛烯醇化物的不对称羟醛反应。用多种双齿芳香醛检查了这种醛醇反应的底物范围，以提供具有高非对映选择性和分离产率的顺醛醇产物。N- (甲苯磺酰基)苯丙氨醇的两种对映异构体都容易由市售且具有光学活性的苯丙氨醇制备。温和皂化去除手性助剂并提供光学活性β-羟基羧酸。