(S)-tert-butyl 4-<(benzyloxycarbonyl)amino>-3-oxo-6-methylheptanoate | 108860-00-0

• 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)-tert-butyl 4-<(benzyloxycarbonyl)amino>-3-oxo-6-methylheptanoate
• 英文别名: t-butyl (S)-4-(benzyloxycarbonylamino)-6-methyl-3-oxo-heptanoate；tert-butyl (4S)-6-methyl-3-oxo-4-(phenylmethoxycarbonylamino)heptanoate
• CAS: 108860-00-0
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: RUPUIMHXGGOHSZ-INIZCTEOSA-N

物化性质

• 沸点：
  476.6±35.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 4-<(benzyloxycarbonyl)amino>-3-oxo-6-methylheptanoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (3S,4S)-4-Benzyloxycarbonylamino-3-hydroxy-6-methyl-heptanoic acid tert-butyl ester 、 (3R,4S)-4-Benzyloxycarbonylamino-3-hydroxy-6-methyl-heptanoic acid tert-butyl ester
  参考文献：
  名称：

  Dufour, Marie-Noelle; Jouin, Patrick; Poncet, Joel, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1895 - 1900

  摘要：

  DOI：
• 作为产物：
  描述：

  醋酸叔丁酯 、 苄氧羰基-亮氨酸甲酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 以98%的产率得到(S)-tert-butyl 4-<(benzyloxycarbonyl)amino>-3-oxo-6-methylheptanoate
  参考文献：
  名称：

  An efficient synthesis of γ-amino β-ketoester by cross-Claisen condensation with α-amino acid derivatives

  摘要：

  Cross-ester condensation between N-protected amino acid ester and the lithium enolate prepared from alkyl acetate gave the corresponding beta-ketoester in high yield without the formation of the tertiary alcohol that is commonly seen as by-product. This interesting reaction is applicable to the amino acid derivatives with suitable N-protecting groups, which can help to stabilize the reaction intermediates. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00464-7

文献信息

• A simple, stereoselective synthesis of ketomethylene dipeptide isosteres
  作者：Robert V. Hoffman、Junhua Tao

  DOI：10.1016/s0040-4020(97)00410-9

  日期：1997.5

  An exceedingly simple, general, and stereoselective method for the preparation of ketomethylene dipeptide isosteres (5-(carbobenzyloxyamino)-2-alkyl-γ-ketoesters) from Cbz-protected amino acids and scalemic 2-triflyloxy esters has been developed. The method is short (three steps), efficient, and highly diastereoselective and enantioselective.

  已经开发了一种非常简单，通用和立体选择性的方法，该方法可从Cbz保护的氨基酸和规模的2-triflyloxy酯制备酮亚甲基二肽等位异构体（5-（羰基苄氧基氨基）-2-烷基-γ-酮酸酯）。该方法是短的（三个步骤），有效的，高度非对映选择性和对映选择性的。
• Dufour, Marie-Noelle; Jouin, Patrick; Poncet, Joel, Journal of the Chemical Society. Perkin transactions I, 1986, p. 1895 - 1900
  作者：Dufour, Marie-Noelle、Jouin, Patrick、Poncet, Joel、Pantaloni, Antoine、Castro, Bertrand

  DOI：——

  日期：——
• An efficient synthesis of γ-amino β-ketoester by cross-Claisen condensation with α-amino acid derivatives
  作者：Yutaka Honda、Satoshi Katayama、Mitsuhiko Kojima、Takayuki Suzuki、Kunisuke Izawa

  DOI：10.1016/s0040-4039(03)00464-7

  日期：2003.4

  Cross-ester condensation between N-protected amino acid ester and the lithium enolate prepared from alkyl acetate gave the corresponding beta-ketoester in high yield without the formation of the tertiary alcohol that is commonly seen as by-product. This interesting reaction is applicable to the amino acid derivatives with suitable N-protecting groups, which can help to stabilize the reaction intermediates. (C) 2003 Elsevier Science Ltd. All rights reserved.