(S)-3-benzyloxycarbonylamino-4,4-dimethylpentanoic acid | 1159138-98-3

• 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: (S)-3-benzyloxycarbonylamino-4,4-dimethylpentanoic acid
• 英文别名: (S)-Cbz-β(3)-neopentylglycine；(S)-3-(((Benzyloxy)carbonyl)amino)-4,4-dimethylpentanoic acid；(3S)-4,4-dimethyl-3-(phenylmethoxycarbonylamino)pentanoic acid
• CAS: 1159138-98-3
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: PAENHBDXAWYRRZ-LBPRGKRZSA-N

物化性质

• 沸点：
  451.6±38.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-3-benzyloxycarbonylamino-4,4-dimethylpentanoic acid 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 50.0 ℃ 、1.0 MPa 条件下， 反应 24.0h， 以94.1%的产率得到(S)-β-neopentyl glycine
  参考文献：
  名称：

  Enantiopure β3-neopentylglycine: synthesis and resolution

  摘要：

  A procedure has been developed for the large scale synthesis of enantiopure beta(3)-neopentylglycine and its Cbz-protected derivative. The synthetic route developed in Out laboratory features Cbz-protection of the racemic beta-amino acid followed by resolution with L-norephedrine and provides the enantiomerically Pure Cbz-beta-neopentylglycine in good yield and excellent enantiopurity. No toxic or dangerous chemicals are used, allowing the scale-up of this procedure without major safety concerns. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.018
• 作为产物：
  描述：

  L-(-)-norephedrine (S)-3-benzyloxycarbonylamino-4,4-dimethylpentanoic acid salt 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 以95.9%的产率得到(S)-3-benzyloxycarbonylamino-4,4-dimethylpentanoic acid
  参考文献：
  名称：

  Enantiopure β3-neopentylglycine: synthesis and resolution

  摘要：

  A procedure has been developed for the large scale synthesis of enantiopure beta(3)-neopentylglycine and its Cbz-protected derivative. The synthetic route developed in Out laboratory features Cbz-protection of the racemic beta-amino acid followed by resolution with L-norephedrine and provides the enantiomerically Pure Cbz-beta-neopentylglycine in good yield and excellent enantiopurity. No toxic or dangerous chemicals are used, allowing the scale-up of this procedure without major safety concerns. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.018

文献信息

• Enantiopure β3-neopentylglycine: synthesis and resolution
  作者：Matthijs K.J. ter Wiel、Mirjam Arnold、Sandra Peter、Ingo Troltsch、Stefan Merget、Florian Glaser、Michael Schwarm、Harjinder S. Bhatti、Biju Kuriakose、Suryakant S. Pol、Mohanasundaram Balamurugan、Viral V. Joshi

  DOI：10.1016/j.tetasy.2009.01.018

  日期：2009.3

  A procedure has been developed for the large scale synthesis of enantiopure beta(3)-neopentylglycine and its Cbz-protected derivative. The synthetic route developed in Out laboratory features Cbz-protection of the racemic beta-amino acid followed by resolution with L-norephedrine and provides the enantiomerically Pure Cbz-beta-neopentylglycine in good yield and excellent enantiopurity. No toxic or dangerous chemicals are used, allowing the scale-up of this procedure without major safety concerns. (c) 2009 Elsevier Ltd. All rights reserved.