((benzyloxy)carbonyl)((3-((2R,3S,4R,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)propyl)sulfonyl)-D-alanine | 1363386-00-8

• 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: ((benzyloxy)carbonyl)((3-((2R,3S,4R,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)propyl)sulfonyl)-D-alanine
• CAS: 1363386-00-8
• 化学式: C₂₈H₃₇NO₁₅S
• 分子量: 659.665
• InChiKey: CZSYSEMFZNUYPH-LHNRFUMQSA-N

物化性质

• 沸点：
  794.9±60.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  45.0
• 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：
  224.2
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  ((benzyloxy)carbonyl)((3-((2R,3S,4R,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)propyl)sulfonyl)-D-alanine 在 1,1-二氯甲醚 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 以70%的产率得到[(2R,3R,4R,5S,6R)-3,4,5-triacetyloxy-6-[3-[[(4R)-2,5-dioxo-1,3-oxazolidin-4-yl]methylsulfonyl]propyl]oxan-2-yl]methyl acetate
  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：

  苄氧羰基半胱氨酸 在 安息香双甲醚 、 双氧水 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 ((benzyloxy)carbonyl)((3-((2R,3S,4R,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)propyl)sulfonyl)-D-alanine
  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