S-Oxo-S<(methylthio)methyl>-D-cysteinol | 77826-61-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: S-Oxo-S<(methylthio)methyl>-D-cysteinol
• 英文别名: S-oxo-S-[(methylthio)methyl]-D-cysteinol；S-Oxo-S[(methylthio)methyl]-D-cysteinol；(2S)-2-amino-3-[(S)-methylsulfanylmethylsulfinyl]propan-1-ol
• CAS: 77826-61-0
• 化学式: C₅H₁₃NO₂S₂
• 分子量: 183.296
• InChiKey: XXKRUXWFOXGFQQ-RRAGMBSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-Oxo-S<(methylthio)methyl>-D-cysteinol 、 3-(2,4-二氧代-6-甲基-5-嘧啶基)丙烯酸 在 氯甲酸乙酯 、 三乙胺 作用下， 生成 S-episparsomycin
  参考文献：
  名称：

  Total synthesis of the antibiotic sparsomycin, a modified uracil amino acid monoxodithioacetal

  摘要：

  DOI：

  10.1021/jo00329a027
• 作为产物：
  描述：

  [(S)-1-Hydroxymethyl-2-((S)-methylsulfanylmethanesulfinyl)-ethyl]-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 反应 1.0h， 以99.1%的产率得到S-Oxo-S<(methylthio)methyl>-D-cysteinol
  参考文献：
  名称：

  Synthesis and biological activity of S-oxo-[(methylthio)-methyl]cysteinols

  摘要：

  A convenient route was developed to synthesize S-oxo-[(methylthio)-methyl]cysteitiols on a large scale from cheap L-serine as the starting material. The structures of diastereoisomers were determined by NMR, CD spectra, and X-ray diffraction analysis. All four diastereoisomers were examined for their ability to inhibit certain bacteria from growing. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.089

文献信息

• Total synthesis of the antibiotic sparsomycin, a modified uracil amino acid monoxodithioacetal
  作者：Harry C. J. Ottenheijm、Rob M. J. Liskamp、Simon P. J. M. Van Nispen、Hans A. Boots、Marian W. Tijhuis

  DOI：10.1021/jo00329a027

  日期：1981.7
• Synthesis and biological activity of S-oxo-[(methylthio)-methyl]cysteinols
  作者：Zhen Xi、Xiao-Feng Cheng、Wen-Bin Chen、Li-Qiang Cao

  DOI：10.1016/j.tetlet.2006.03.089

  日期：2006.5

  A convenient route was developed to synthesize S-oxo-[(methylthio)-methyl]cysteitiols on a large scale from cheap L-serine as the starting material. The structures of diastereoisomers were determined by NMR, CD spectra, and X-ray diffraction analysis. All four diastereoisomers were examined for their ability to inhibit certain bacteria from growing. (c) 2006 Elsevier Ltd. All rights reserved.