{(1S)-1-[(1S)-3-methyl-1-(2-oxoethyl)butylcarbamoyl]-2-phenylethyl}carbamic acid benzyl ester | 1360566-30-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {(1S)-1-[(1S)-3-methyl-1-(2-oxoethyl)butylcarbamoyl]-2-phenylethyl}carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-1-[[(3S)-5-methyl-1-oxohexan-3-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 1360566-30-8
• 化学式: C₂₄H₃₀N₂O₄
• 分子量: 410.513
• InChiKey: OMSZQIJZQWTXIK-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1-methoxy-3-methylbutyl)carbamic acid tert-butyl ester 在 盐酸 、 水 、 四氯化锡 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 49.25h， 生成 {(1S)-1-[(1S)-3-methyl-1-(2-oxoethyl)butylcarbamoyl]-2-phenylethyl}carbamic acid benzyl ester
  参考文献：
  名称：

  Access to C-protected β-amino-aldehydes via transacetalization of 6-alcoxy tetrahydrooxazinones and use for pseudo-peptide synthesis

  摘要：

  Efficient access to masked beta-amino-aldehydes was performed starting from 6-alcoxy tetrahydrooxazinone 6a-d (6-ATO). Transacetalization leads to the opening of the cycle to form either unsymmetric acetal 7 or symmetric acetals 16-18. These amino acetals are key compounds, obtained with 99% ee, which can be engaged in efficient peptide coupling. This method could easily provide peptides aldehydes or small amido aldehydes as exemplified with the formal synthesis of ent-Maraviroc. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.002

文献信息

• Access to C-protected β-amino-aldehydes via transacetalization of 6-alcoxy tetrahydrooxazinones and use for pseudo-peptide synthesis
  作者：Pavlo Shpak-Kraievskyi、Biaolin Yin、Arnaud Martel、Robert Dhal、Gilles Dujardin、Mathieu Y. Laurent

  DOI：10.1016/j.tet.2012.01.002

  日期：2012.3

  Efficient access to masked beta-amino-aldehydes was performed starting from 6-alcoxy tetrahydrooxazinone 6a-d (6-ATO). Transacetalization leads to the opening of the cycle to form either unsymmetric acetal 7 or symmetric acetals 16-18. These amino acetals are key compounds, obtained with 99% ee, which can be engaged in efficient peptide coupling. This method could easily provide peptides aldehydes or small amido aldehydes as exemplified with the formal synthesis of ent-Maraviroc. (C) 2012 Elsevier Ltd. All rights reserved.