tert-butyl (3S,5S,6R)-3-[(3R)-4-azido-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate | 753010-16-1

• 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-[(3R)-4-azido-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate
• 英文别名: tert-butyl (3S,5S,6R)-3-[(R)-4-azido-3-hydroxybutyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate；tert-butyl (3S,5S,6R)-3-((R)4-azido-3-hydroxybutyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate；tert-butyl (3S,5S,6R)-3-[(3R)-4-azido-3-hydroxybutyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 753010-16-1
• 化学式: C₂₅H₃₀N₄O₅
• 分子量: 466.537
• InChiKey: QLSZXBXXOPPQES-CLAROIROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  90.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,5S,6R)-3-[(3R)-4-azido-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate 在 palladium on activated charcoal 、 palladium dichloride 盐酸 、 氢气 、 氧气 、 sodium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 zinc dibromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 149.0h， 生成 pyridinoline tetrahydrochloride
  参考文献：
  名称：

  Practical Syntheses of Pyridinolines, Important Amino Acidic Biomarkers of Collagen Health

  摘要：

  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.

  DOI：

  10.1021/jo070136g
• 作为产物：
  描述：

  (2R,3S)-(-)-N-Boc-2,3-二苯基-6-氧代吗啉 在 六甲基磷酰三胺 、 sodium azide 、 氯化铵 、 间氯过氧苯甲酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 二氯甲烷 、 乙二醇甲醚 为溶剂， 反应 32.75h， 生成 tert-butyl (3S,5S,6R)-3-[(3R)-4-azido-3-hydroxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate
  参考文献：
  名称：

  细菌二异腈酯SF2768的全合成。

  摘要：

  Chalkophores是细菌的天然产物，可螯合和转运细胞外铜。二异腈腈天然产物SF2768首先作为抗真菌抗生素从链霉菌属物种中分离出来，最近被表征为细菌生粉团和潜在的致病因子。在这里，我们报告SF2768和相关的无环类似物的模块合成，允许整个中央乳醇环的顺式立体化学的分配。还已经研究了这些二腈的铜结合性能。

  DOI：

  10.1021/acs.orglett.9b03348

文献信息

• 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
  作者：Pietro Allevi、Mario Anastasia

  DOI：10.1016/j.tetasy.2004.06.004

  日期：2004.7

  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.
• Total Synthesis of the Bacterial Diisonitrile Chalkophore SF2768
  作者：Yao Xu、Derek S. Tan

  DOI：10.1021/acs.orglett.9b03348

  日期：2019.11.1

  has more recently been characterized as a bacterial chalkophore and potential virulence factor. Herein, we report a modular synthesis of SF2768 and related acyclic analogues, allowing assignment of syn-stereochemistry across the central lactol ring. The copper-binding properties of these diisonitriles have also been studied.

  Chalkophores是细菌的天然产物，可螯合和转运细胞外铜。二异腈腈天然产物SF2768首先作为抗真菌抗生素从链霉菌属物种中分离出来，最近被表征为细菌生粉团和潜在的致病因子。在这里，我们报告SF2768和相关的无环类似物的模块合成，允许整个中央乳醇环的顺式立体化学的分配。还已经研究了这些二腈的铜结合性能。
• 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.