(3S,5S,6R)-3-(3-丁烯基)-2-氧代-5,6-二苯基-4-吗啉羧酸叔-丁酯 | 144542-72-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (3S,5S,6R)-3-(3-丁烯基)-2-氧代-5,6-二苯基-4-吗啉羧酸叔-丁酯
• 英文名称: (3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
• 英文别名: (3S,5S,6R)-4-(tert-butoxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one；tert-butyl (3S,5S,6R)-3-(but-3-en-1-yl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate；tert-butyl (3S,5S,6R)-3-(3-butenyl)-2-oxo-5,6-diphenyl-1,4-oxazine-4-carboxylate；(3S,5S,6R)-3-(3-Butenyl)-2-oxo-5,6-diphenyl-4-morpholinecarboxylic Acid tert-Butyl Ester；tert-butyl (3S,5S,6R)-3-but-3-enyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate
• CAS: 144542-72-3
• 化学式: C₂₅H₂₉NO₄
• 分子量: 407.51
• InChiKey: XUZJKECLNPPVLC-FDFHNCONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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 sodium azide 、 phosphate buffer 、 氯化铵 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 乙二醇甲醚 、 水 、 1,2-二氯乙烷 为溶剂， 反应 41.5h， 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：

  4-碘-1-丁烯 、 (2R,3S)-(-)-N-Boc-2,3-二苯基-6-氧代吗啉 在 六甲基磷酰三胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到(3S,5S,6R)-3-(3-丁烯基)-2-氧代-5,6-二苯基-4-吗啉羧酸叔-丁酯
  参考文献：
  名称：

  （2S，3S，6S）-，（2S，3S，6R）-和（2R，3R，6S）-2,3-Methano-2,6-二氨基庚二酸的不对称合成。直接针对新型L，L-二氨基庚二酸酯差向异构酶底物抑制剂设计的研究

  摘要：

  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。

  DOI：

  10.1016/0040-4020(95)00976-0

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。
• Asymmetric synthesis of 2,6-diaminopimelic acids
  作者：Robert M. Williams、Chenguang Yuan

  DOI：10.1021/jo00050a028

  日期：1992.11

  The preparations of (RR)-2,6-diaminopimelic acid, (S,S)-2,6-diaminopimelic acid, (SR)-2,6-diaminopimelic acid, and (SS)-2,7-diaminosuberic acid are described. The synthesis of mono-N-protected (SR)-2,6-diaminopimelic acid is also described.
• 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.