(3S,4S,6R,9S)-3-amino-1-aza-2-oxo-4-hydroxymethyl-bicyclo[4.3.0]nonanecarboxylic acid tert-butyl ester | 851544-54-2

• 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: (3S,4S,6R,9S)-3-amino-1-aza-2-oxo-4-hydroxymethyl-bicyclo[4.3.0]nonanecarboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3S,6S,7S,8aR)-6-amino-7-(hydroxymethyl)-5-oxo-2,3,6,7,8,8a-hexahydro-1H-indolizine-3-carboxylate
• CAS: 851544-54-2
• 化学式: C₁₄H₂₄N₂O₄
• 分子量: 284.356
• InChiKey: GURZIJILJKEUOJ-ZNSHCXBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S,6R,9S)-3-amino-1-aza-2-oxo-4-hydroxymethyl-bicyclo[4.3.0]nonanecarboxylic acid tert-butyl ester 在 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 18.75h， 生成 (3S,6S,7S,8aR)-6-Benzyloxycarbonylamino-7-methanesulfonyloxymethyl-5-oxo-octahydro-indolizine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  单击化学以使拟肽功能化

  摘要：

  Sharpless改性的Huisgen叠氮化物和炔属衍生物的[2 + 3]环加成反应是一种有效且简单的方法，可将amobi-Ser-Pro二肽类似物的氮杂双环烷氨基酸与生物学相关的伴侣偶联。

  DOI：

  10.1016/j.tetlet.2006.03.149
• 作为产物：
  描述：

  (3aS,4aR,7R,8aS)-1-benzyl-8-oxo-octahydro-2-oxa-1,7a-diaza-s-indacene-7-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以99%的产率得到(3S,4S,6R,9S)-3-amino-1-aza-2-oxo-4-hydroxymethyl-bicyclo[4.3.0]nonanecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Functionalized Azabicycloalkane Amino Acids by Nitrone 1,3-Dipolar Intramolecular Cycloaddition

  摘要：

  An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.

  DOI：

  10.1021/jo0500683

文献信息

• WO2006/92722
  申请人：——

  公开号：——

  公开（公告）日：——
• Peptidomimetic Compounds and Preparation of Biologically Active Derivatives
  申请人：Scolastico Carlo

  公开号：US20080139461A1

  公开（公告）日：2008-06-12

  The invention relates to novel cyclic peptidomimetic compounds containing the sequence RGD for the preparation of appropriately functionalised antagonists of αvβ3 and αvβ5 integrins, and intended, for example, for the treatment of altered angiogenic phenomena or for the preparation of diagnostically useful compounds.
• Click chemistry to functionalise peptidomimetics
  作者：Daniela Arosio、Matteo Bertoli、Leonardo Manzoni、Carlo Scolastico

  DOI：10.1016/j.tetlet.2006.03.149

  日期：2006.5

  Sharpless modified Huisgen’s [2+3] cycloaddition of azide and acetylenic derivatives was employed as an efficient and simple method to conjugate azabicycloalkane amino acids, mimics of a homoSer-Pro dipeptide, with biologically relevant partners.

  Sharpless改性的Huisgen叠氮化物和炔属衍生物的[2 + 3]环加成反应是一种有效且简单的方法，可将amobi-Ser-Pro二肽类似物的氮杂双环烷氨基酸与生物学相关的伴侣偶联。
• Functionalized Azabicycloalkane Amino Acids by Nitrone 1,3-Dipolar Intramolecular Cycloaddition
  作者：Leonardo Manzoni、Daniela Arosio、Laura Belvisi、Antonio Bracci、Matteo Colombo、Donatella Invernizzi、Carlo Scolastico

  DOI：10.1021/jo0500683

  日期：2005.5.1

  An efficient and operationally simple method for the synthesis of functionalized azaoxobicyclo[X.3.0]alkane amino acids has been devised. The key step is an intramolecular nitrone cycloaddition on 5-allyl- or 5-homoallylproline that was found to be completely regio- and stereoselective.