N-((benzyloxy)carbonyl)-S-(3-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)propyl)-L-cysteine | 1363385-96-9

• 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: N-((benzyloxy)carbonyl)-S-(3-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)propyl)-L-cysteine
• CAS: 1363385-96-9
• 化学式: C₂₈H₃₇NO₁₃S
• 分子量: 627.667
• InChiKey: NSSGTFLTUWUYEV-GKLJYDMOSA-N

物化性质

• 沸点：
  728.2±60.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  190.06
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-((benzyloxy)carbonyl)-S-(3-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)propyl)-L-cysteine 在 1,1-二氯甲醚 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以63%的产率得到(2R,3S,4R,5S,6R)-2-(acetoxymethyl)-6-(3-((((R)-2,5-dioxooxazolidin-4-yl)methyl)thio)propyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Glycopolypeptides with a Redox-Triggered Helix-to-Coil Transition

  摘要：

  Conformation-switchable glycopolypeptides were prepared by the living polymerization of glycosylated L-cysteine-N-carboxyanhydride (glyco-C NCA) monomers. These new monomers were prepared in high yield by coupling of alkene-terminated C-linked glycosides of D-galactose or ID-glucose to L-cysteine using thiol-ene "click" chemistry, followed by their conversion to the corresponding glyco-C NCAs. The resulting glycopolypeptides were found to be water-soluble and alpha-helical in solution. Aqueous oxidation of the side-chain thioether linkages in these polymers to sulfone groups resulted in disruption of the a-helical conformations without loss of water solubility. The ability to switch chain conformation and remain water-soluble is unprecedented in synthetic polymers, and allows new capabilities to control presentation of sugar functionality in subtly different contexts.

  DOI：

  10.1021/ja3007484
• 作为产物：
  描述：

  氯甲酸苄酯 在 安息香双甲醚 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.25h， 生成 N-((benzyloxy)carbonyl)-S-(3-((2R,3S,4R,5S,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)propyl)-L-cysteine
  参考文献：
  名称：

  Glycopolypeptides with a Redox-Triggered Helix-to-Coil Transition

  摘要：

  Conformation-switchable glycopolypeptides were prepared by the living polymerization of glycosylated L-cysteine-N-carboxyanhydride (glyco-C NCA) monomers. These new monomers were prepared in high yield by coupling of alkene-terminated C-linked glycosides of D-galactose or ID-glucose to L-cysteine using thiol-ene "click" chemistry, followed by their conversion to the corresponding glyco-C NCAs. The resulting glycopolypeptides were found to be water-soluble and alpha-helical in solution. Aqueous oxidation of the side-chain thioether linkages in these polymers to sulfone groups resulted in disruption of the a-helical conformations without loss of water solubility. The ability to switch chain conformation and remain water-soluble is unprecedented in synthetic polymers, and allows new capabilities to control presentation of sugar functionality in subtly different contexts.

  DOI：

  10.1021/ja3007484