(2S,3R)-1-[(4S)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-hydroxy-2-methyloctadecan-1-one | 937242-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (2S,3R)-1-[(4S)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-hydroxy-2-methyloctadecan-1-one
• CAS: 937242-52-9
• 化学式: C₂₉H₄₇NO₂S₂
• 分子量: 505.83
• InChiKey: ZWODSXMMODTILO-DOEKTCAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  34
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1-[(4S)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-hydroxy-2-methyloctadecan-1-one 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 25.5h， 生成 (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 、 1-[(4R)-4-(苯基甲基)-2-硫代-3-噻唑烷基]-1-丙酮 在 鹰爪豆碱 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 以45%的产率得到(2S,3R)-1-[(4S)-4-benzyl-2-sulfanylidene-1,3-thiazolidin-3-yl]-3-hydroxy-2-methyloctadecan-1-one
  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 and Stereochemical Assignment of Brasilibactin A
  作者：Judith M. Mitchell、Jared T. Shaw

  DOI：10.1021/ol070355o

  日期：2007.4.1

  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.