di-N,N-(tert-butyloxycarbonyl)-D-cystinol | 82459-46-9

• 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: di-N,N-(tert-butyloxycarbonyl)-D-cystinol
• 英文别名: Boc-D-Cys(1)-ol.Boc-D-Cys(1)-ol；tert-butyl N-[(2S)-1-hydroxy-3-[[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]disulfanyl]propan-2-yl]carbamate
• CAS: 82459-46-9
• 化学式: C₁₆H₃₂N₂O₆S₂
• 分子量: 412.572
• InChiKey: FRXTXGMKJVJBAI-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  168
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  di-N,N-(tert-butyloxycarbonyl)-D-cystinol 在 吡啶 、 N-氯代丁二酰亚胺 、 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 为溶剂， 生成 [(S)-1-Hydroxymethyl-2-((S)-methylsulfanylmethanesulfinyl)-ethyl]-carbamic acid tert-butyl ester
  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
• 作为产物：
  描述：

  [(S)-3-(tert-butoxycarbonyl)-2-oxooxazolidin-4-yl]methyl-4-methylbenzenesulfonate 在 N-羟基丁二酰亚胺 、 caesium carbonate 、 sodium iodide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 8.0h， 生成 di-N,N-(tert-butyloxycarbonyl)-D-cystinol
  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

• Synthesis of the Alkylsulfonate Metabolites Cysteinolic Acid, 3-Amino-2-hydroxypropanesulfonate, and 2,3-Dihydroxypropanesulfonate
  作者：Laura Burchill、Luca Zudich、Phillip L. van der Peet、Jonathan M. White、Spencer J. Williams

  DOI：10.1021/acs.joc.2c00036

  日期：2022.3.18

  Chiral hydroxy- and aminohydroxysulfonic acids are widespread in the marine and terrestrial environment. Here we report simple methods for the synthesis of d- and l-cysteinolic acid (from (Boc-d-Cys-OH)2 and (Boc-l-Cys-OH)2, respectively), R- and S-3-amino-2-hydroxypropanesulfonate (from S- and R-epichlorohydrin, respectively), and R- and S-2,3-dihydroxypropanesulfonate (from S- and R-epichlorohydrin

  手性羟基和氨基羟基磺酸广泛存在于海洋和陆地环境中。在这里，我们报告了合成d - 和l -半胱氨酸（分别来自 (Boc- d -Cys-OH) 2和 (Boc- l -Cys-OH) 2）、R - 和S -3-的简单方法氨基-2-羟基丙磺酸盐（分别来自S-和R-表氯醇），以及R-和S -2,3-二羟基丙磺酸盐（分别来自S-和R-表氯醇）。d-半胱氨酸胆汁盐是通过与胆酸和鹅去氧胆酸偶联产生的。一系列单晶 3D X 射线结构证实了氨基磺酸盐的绝对构型。通过比较旋光度，我们将来自Gateloupia livida的天然存在的 3-氨基-2-羟基丙磺酸盐指定为具有R构型。这种简单的合成方法将支持未来对这些烷基磺酸盐的发生、化学分类分布和代谢的研究。
• 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.