(2S,5R)-2-amino-6[(2R,5S)-5-amino-5-carboxy-2-hydroxypentylamino]-5-hydroxyhexanoic acid | 869111-52-4

• 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: (2S,5R)-2-amino-6[(2R,5S)-5-amino-5-carboxy-2-hydroxypentylamino]-5-hydroxyhexanoic acid
• 英文别名: (5R,5'R)-Dihydroxy Lysinonorleucine；(2S,5R)-2-amino-6-[[(2R,5S)-5-amino-5-carboxy-2-hydroxypentyl]amino]-5-hydroxyhexanoic acid
• CAS: 869111-52-4
• 化学式: C₁₂H₂₅N₃O₆
• 分子量: 307.347
• InChiKey: COYAOJMPFAKKAM-IMSYWVGJSA-N

物化性质

• 熔点：
  >240°C (dec.)
• 沸点：
  640.3±55.0 °C(Predicted)
• 密度：
  1.344±0.06 g/cm3(Predicted)
• 溶解度：
  可微溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -7.2
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  tert-butyl (3S,5S,6R)-3-[(3R)-4-[benzyl-[(2R)-2-hydroxy-4-[(3S,5S,6R)-4-[(2-methylpropan-2-yl)oxycarbonyl]-2-oxo-5,6-diphenylmorpholin-3-yl]butyl]amino]-3-hydroxybutyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate 在 氢气 、 palladium dichloride 、 zinc dibromide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 51.0h， 生成 (2S,5R)-2-amino-6[(2R,5S)-5-amino-5-carboxy-2-hydroxypentylamino]-5-hydroxyhexanoic acid
  参考文献：
  名称：

  Reduced collagen cross links: the first synthesis of all the possible (2S,2′S)-stereoisomers of 5-hydroxylysinonorleucine and of 5,5′-dihydroxylysinonorleucine in enantiomerically pure form

  摘要：

  The paper reports the first enantioselective synthesis of all the possible collagen reduced cross links as described: (2S,2'S,5R)- and (2S,2S,5S)-5-hydroxylysinonorleucine 3a and 3b, (2S,2'S,5R,5'R)-5,5'-dihydroxylysinonorleucine 4a, (2S,2'S, 5R,5'S)-5,5'-dihydroxylysinonorleucine 4b and (2S,2'S,5S,5'S)-5,5'-dihydroxylysinonorleucine 4c. The Williams' glycine template methodology was used both for the introduction of a stereogenic at the alpha-position and for an easy protection of the amino acidic functionalities during the synthesis of the dimeric amino acids. (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.08.023

文献信息

• Reduced collagen cross links: the first synthesis of all the possible (2S,2′S)-stereoisomers of 5-hydroxylysinonorleucine and of 5,5′-dihydroxylysinonorleucine in enantiomerically pure form
  作者：Riccardo Cribiù、Pietro Allevi、Mario Anastasia

  DOI：10.1016/j.tetasy.2005.08.023

  日期：2005.9

  The paper reports the first enantioselective synthesis of all the possible collagen reduced cross links as described: (2S,2'S,5R)- and (2S,2S,5S)-5-hydroxylysinonorleucine 3a and 3b, (2S,2'S,5R,5'R)-5,5'-dihydroxylysinonorleucine 4a, (2S,2'S, 5R,5'S)-5,5'-dihydroxylysinonorleucine 4b and (2S,2'S,5S,5'S)-5,5'-dihydroxylysinonorleucine 4c. The Williams' glycine template methodology was used both for the introduction of a stereogenic at the alpha-position and for an easy protection of the amino acidic functionalities during the synthesis of the dimeric amino acids. (C) 2005 Published by Elsevier Ltd.