tert-butyl (3S,5S,6R)-3-[(3S)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate | 753010-19-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: tert-butyl (3S,5S,6R)-3-[(3S)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate
• 英文别名: tert-butyl (3S,5S,6R)-3-[(3S)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 753010-19-4
• 化学式: C₂₅H₃₀INO₅
• 分子量: 551.421
• InChiKey: GRXWENAIZYMJDI-MYGLTJDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,5S,6R)-3-[(3S)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate 在 sodium azide 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 (2S,5S)-5-hydroxylysine hydrochloride
  参考文献：
  名称：

  A practical and simple synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine and of a related α-amino acid required for the synthesis of the collagen cross-link pyridinoline

  摘要：

  A four step synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine using Williams' glycine template methodology for controlling the stereogenicity at the alpha-position is reported. This route offers the possibility for the synthesis of all possible isomers of 5-hydroxylysine and of an important alpha-amino acidic iodohydrin required for the construction of the hydroxylated side chain of the collagen cross-link pyridinoline. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.004
• 作为产物：
  描述：

  (3S,5S,6R)-3-(3-丁烯基)-2-氧代-5,6-二苯基-4-吗啉羧酸叔-丁酯 在 phosphate buffer 、 溶剂黄146 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 13.0h， 生成 tert-butyl (3S,5S,6R)-3-[(3S)-3-hydroxy-4-iodobutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate
  参考文献：
  名称：

  A practical and simple synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine and of a related α-amino acid required for the synthesis of the collagen cross-link pyridinoline

  摘要：

  A four step synthesis of (2S,5R)- and (2S,5S)-5-hydroxylysine using Williams' glycine template methodology for controlling the stereogenicity at the alpha-position is reported. This route offers the possibility for the synthesis of all possible isomers of 5-hydroxylysine and of an important alpha-amino acidic iodohydrin required for the construction of the hydroxylated side chain of the collagen cross-link pyridinoline. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.004

文献信息

• Practical Syntheses of Pyridinolines, Important Amino Acidic Biomarkers of Collagen Health
  作者：Pietro Allevi、Riccardo Cribiù、Elios Giannini、Mario Anastasia

  DOI：10.1021/jo070136g

  日期：2007.4.1

  The paper reports some successful results on the first fully stereoselective total synthesis of the collagen cross-link pyridinolines. All stereogenic centers are stereoselectively introduced using Williams glycine template methodology, and oxazinones are used as a source of chirality and as easily removable protecting groups of the amino acidic functionalities during the assembly of the pyridinoline nucleus.