2'-methanesulfonyloxyethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside | 72718-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-methanesulfonyloxyethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
• CAS: 72718-00-4
• 化学式: C₁₄H₂₂O₁₁S
• 分子量: 398.388
• InChiKey: URBFLVWWDDZOGW-XJFOESAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.87
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  140.73
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2'-methanesulfonyloxyethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到2'-azidoethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  “Click” Glycodendrimers Containing 27, 81, and 243 Modified Xylopyranoside Termini

  摘要：

  A series of large glycodendrimers containing 27, 81, and 243 terminal modified xylose branches from the first (G(1)-27) to the third generation (G(3)-243) were synthesized from 2'-azidoethyl 2,3,4-tri-O-acetyl-beta-D-xylopyranoside and alkynyl-terminated dendrimers by "click" chemistry that is confirmed to be an excellent method to obtain large glyco-dendtimers exemplified by the use of modified xylose. The dendrimers were first characterized by H-1 NMR, C-13{H-1} NMR, elemental analysis, and IR spectroscopy. The size progression in the series was also demonstrated using both DOSY NMR and size exclusion chromatography (SEC), the latter technique showing the good polydispersity of all the dendrimers. The size measured by dynamic light scattering (DLS) for the dendrimer G(3)-243 is close to that obtained by the DOSY NMR method.

  DOI：

  10.1021/jo900554b
• 作为产物：
  描述：

  2-hydroxyethyl 2,3,4-tri-O-acetyl-β-D-xylopyranose 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到2'-methanesulfonyloxyethyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside
  参考文献：
  名称：

  “Click” Glycodendrimers Containing 27, 81, and 243 Modified Xylopyranoside Termini

  摘要：

  A series of large glycodendrimers containing 27, 81, and 243 terminal modified xylose branches from the first (G(1)-27) to the third generation (G(3)-243) were synthesized from 2'-azidoethyl 2,3,4-tri-O-acetyl-beta-D-xylopyranoside and alkynyl-terminated dendrimers by "click" chemistry that is confirmed to be an excellent method to obtain large glyco-dendtimers exemplified by the use of modified xylose. The dendrimers were first characterized by H-1 NMR, C-13{H-1} NMR, elemental analysis, and IR spectroscopy. The size progression in the series was also demonstrated using both DOSY NMR and size exclusion chromatography (SEC), the latter technique showing the good polydispersity of all the dendrimers. The size measured by dynamic light scattering (DLS) for the dendrimer G(3)-243 is close to that obtained by the DOSY NMR method.

  DOI：

  10.1021/jo900554b