[(2S,3R)-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-(phenylmethoxycarbonylamino)hexanoate | 937242-56-3

• 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: [(2S,3R)-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-(phenylmethoxycarbonylamino)hexanoate
• CAS: 937242-56-3
• 化学式: C₆₂H₉₈N₄O₁₀Si₂
• 分子量: 1115.65
• InChiKey: KIBHFEFLDSFITM-GRYUQROQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.17
• 重原子数：
  78
• 可旋转键数：
  40
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2S,3R)-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-(phenylmethoxycarbonylamino)hexanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以51%的产率得到(2S,3R)-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
• 作为产物：
  描述：

  十六醛 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 27.17h， 生成 [(2S,3R)-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-(phenylmethoxycarbonylamino)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

文献信息

• Synthesis of brasilibactin A and confirmation of absolute configuration of β-hydroxy acid fragment
  作者：Yongcheng Ying、Jiyong Hong

  DOI：10.1016/j.tetlet.2007.09.112

  日期：2007.11

  A synthesis of brasilibactin A, a cytotoxic siderophore from the actinomycete of Nocardia brasiliensis, and three unnatural diastereomers of the natural product is described. Four possible diastereomers of the β-hydroxy acid fragment were prepared via asymmetric aldol reactions and used to synthesize brasilibactin A and its diastereomers. Careful analysis of 1H NMR data confirmed that brasilibactin

  描述了巴西巴西诺卡氏菌放线菌的细胞毒性铁载体Brasilibactin A和天然产物的三种非天然非对映异构体的合成。通过不对称醛醇缩合反应制备了四种可能的β-羟酸片段的非对映异构体，并用于合成brasilibactin A及其非对映异构体。仔细分析1 H NMR数据证实，brasilibactin A具有17 S，18 R绝对立体化学。