(2S,3R)-3-Hydroxy-2,5-dimethyl-hexanoic acid (S)-3-methyl-2-(toluene-4-sulfonylamino)-butyl ester | 479483-91-5

• 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,3R)-3-Hydroxy-2,5-dimethyl-hexanoic acid (S)-3-methyl-2-(toluene-4-sulfonylamino)-butyl ester
• 英文别名: [(2S)-3-methyl-2-[(4-methylphenyl)sulfonylamino]butyl] (2S,3R)-3-hydroxy-2,5-dimethylhexanoate
• CAS: 479483-91-5
• 化学式: C₂₀H₃₃NO₅S
• 分子量: 399.552
• InChiKey: VMJPZXAEVPBATN-QXAKKESOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-Hydroxy-2,5-dimethyl-hexanoic acid (S)-3-methyl-2-(toluene-4-sulfonylamino)-butyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 (2S,3R)-3-hydroxy-2,5-dimethylhexanoic acid
  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：

  (S)-N-(1-hydroxy-3-methylbutan-2-yl)-4-methylbenzenesulfonamide 在 四氯化钛 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S,3R)-3-Hydroxy-2,5-dimethyl-hexanoic acid (S)-3-methyl-2-(toluene-4-sulfonylamino)-butyl ester
  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

• Chelation-controlled ester-derived titanium enolate aldol reaction: diastereoselective syn-aldols with mono- and bidentate aldehydes
  作者：Arun K Ghosh、Jae-Hun Kim

  DOI：10.1016/s0040-4039(02)01113-9

  日期：2002.8

  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.