tert-butyl (3S,5S,6R)-3-(2-((RS)oxiran-2-yl)ethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate | 937183-38-5

• 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-(2-((RS)oxiran-2-yl)ethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• 英文别名: tert-butyl (3S,5S,6R)-3-[3,4-epoxybutyl]-2-oxo-5,6-diphenyl-1,4-oxazinane-4-carboxylate；tert-butyl (3S,5S,6R)-3-(3,4-epoxybutyl)-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate；tert-butyl (3S,5S,6R)-3-[2-(oxiran-2-yl)ethyl]-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 937183-38-5
• 化学式: C₂₅H₂₉NO₅
• 分子量: 423.509
• InChiKey: BFHBDHFYJHFJKI-GEIYVISESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (3S,5S,6R)-3-(2-((RS)oxiran-2-yl)ethyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate 在 sodium azide 、 氯化铵 、 三氟乙酸 作用下， 以 乙二醇甲醚 、 水 为溶剂， 反应 29.5h， 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 间氯过氧苯甲酸 作用下， 以 aq. phosphate buffer 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 tert-butyl (3S,5S,6R)-3-(2-((RS)oxiran-2-yl)ethyl)-2-oxo-5,6-diphenylmorpholine-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

• Asymmetric Syntheses of (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-Methano-2,6-diaminopimelic Acids. Studies Directed to the Design of Novel Substrate-based Inhibitors of L,L-Diaminopimelate Epimerase
  作者：Robert M. Williams、Glenn J. Fegley、Reneé Gallegos、Felicity Schaefer、David L. Pruess

  DOI：10.1016/0040-4020(95)00976-0

  日期：1996.1

  The asymmetric syntheses ot (2S,3S,6S)-, (2S,3S,6R)-, and (2R,3R,6S)-2,3-methano-2,6-diaminopimelic acids (7a-c) is described. The synthesis features phosphonate coupling of 13 and 14 to form the corresponding E-olefins which are subsequently cyclopropanated and deprotected under dissolving metal conditions.

  描述了（2S，3S，6S）-，（2S，3S，6R）-和（2R，3R，6S）-2,3-甲基-2,6-二氨基庚二酸（7a-c）的不对称合成。该合成的特征是13和14的膦酸酯偶联形成相应的E-烯烃，随后将其环丙烷化并在溶解金属条件下脱保护。
• 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.
• 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。
• 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.