(2R,3S)-1-(((R)-1-((tert-butyldiphenylsilyl)oxy)-2-oxoazepan-3-yl)amino)-2-methyl-1-oxooctadecan-3-yl (R)-13-amino-8-formyl-2,2-dimethyl-5,7-dioxa-8-aza-2-silatetradecan-14-oate | 937242-46-1

• 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: (2R,3S)-1-(((R)-1-((tert-butyldiphenylsilyl)oxy)-2-oxoazepan-3-yl)amino)-2-methyl-1-oxooctadecan-3-yl (R)-13-amino-8-formyl-2,2-dimethyl-5,7-dioxa-8-aza-2-silatetradecan-14-oate
• CAS: 937242-46-1
• 化学式: C₅₄H₉₂N₄O₈Si₂
• 分子量: 981.517
• InChiKey: JGJYLKRIQBKMQK-AYHMFJGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  68.0
• 可旋转键数：
  35.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  149.73
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,3S)-1-(((R)-1-((tert-butyldiphenylsilyl)oxy)-2-oxoazepan-3-yl)amino)-2-methyl-1-oxooctadecan-3-yl (R)-13-amino-8-formyl-2,2-dimethyl-5,7-dioxa-8-aza-2-silatetradecan-14-oate 、 (4R)-2-[2-hydroxyphenyl]-Δ²-1,3-oxazoline-4-carboxylic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以50%的产率得到[(2R,3S)-1-[[(3R)-1-[tert-butyl(diphenyl)silyl]oxy-2-oxoazepan-3-yl]amino]-2-methyl-1-oxooctadecan-3-yl] (2R)-6-[formyl(2-trimethylsilylethoxymethoxy)amino]-2-[[(4R)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-oxazole-4-carbonyl]amino]hexanoate
  参考文献：
  名称：

  Synthesis and Stereochemical Assignment of Brasilibactin A

  摘要：

  Brasilibactin A, a naturally occurring siderophore related to the mycobactins, has been synthesized in six steps. Use of asymmetric titanium-mediated aldol reactions allowed the preparation of both diastereomers from a common synthetic intermediate, thus allowing the relative stereochemistry of the natural product to be assigned. Brasilibactin A exhibits no inhibition of histone deacetylases (HDACs) in spite of the N-formyl-N-hydroxy lysine moiety that is expected to affect the activity of these metal-dependent lysine-modifying enzymes.

  DOI：

  10.1021/ol070355o
• 作为产物：
  描述：

  十六醛 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 29.17h， 生成 (2R,3S)-1-(((R)-1-((tert-butyldiphenylsilyl)oxy)-2-oxoazepan-3-yl)amino)-2-methyl-1-oxooctadecan-3-yl (R)-13-amino-8-formyl-2,2-dimethyl-5,7-dioxa-8-aza-2-silatetradecan-14-oate
  参考文献：
  名称：

  Synthesis and Stereochemical Assignment of Brasilibactin A

  摘要：

  Brasilibactin A, a naturally occurring siderophore related to the mycobactins, has been synthesized in six steps. Use of asymmetric titanium-mediated aldol reactions allowed the preparation of both diastereomers from a common synthetic intermediate, thus allowing the relative stereochemistry of the natural product to be assigned. Brasilibactin A exhibits no inhibition of histone deacetylases (HDACs) in spite of the N-formyl-N-hydroxy lysine moiety that is expected to affect the activity of these metal-dependent lysine-modifying enzymes.

  DOI：

  10.1021/ol070355o