methyl 4,6-O-benzylidene-2,3-di-O-(p-toluenesulfonyloxyethyl)-α-D-glucopyranoside | 71088-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4,6-O-benzylidene-2,3-di-O-(p-toluenesulfonyloxyethyl)-α-D-glucopyranoside
• CAS: 71088-79-4
• 化学式: C₃₂H₃₈O₁₂S₂
• 分子量: 678.779
• InChiKey: KRETVKMPFMHEQT-OXODEJSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  46.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N,N′,N′′-三(对甲苯磺酰)二乙撑三胺 、 methyl 4,6-O-benzylidene-2,3-di-O-(p-toluenesulfonyloxyethyl)-α-D-glucopyranoside 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以76%的产率得到methyl 4,6-O-benzylidene-2,3-O-(3,6,9-tritosyl-3,6,9-triiazaundecylene)-α-D-glucopyranoside
  参考文献：
  名称：

  Carbohydrate-based aza-macrocycles by Richman-Atkins cyclization of glucopyranose precursors

  摘要：

  2, 3-Di-omega-halo-as well as 2, 3-di-omega-toluenesulfonamide-alkylated glucopyranoside derivatives were prepared. Their condensation with alpha,omega-bis-toluenesulfonamide components under varying Richman Atkins conditions with alkali carbonate in DMF led to carbohydrate-linked aza-macrocycles displaying 14-, 17-, 18-, 21-, 24-, and 25-membered ring structures. Isomeric aza-macrocylic coronands of 20-as well as 30-membered ring size containing two saccharides could be obtained employing Richman-Atkins condensations of two functionalized sugar building units. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2016.11.016
• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2,3-di-O-(tert-butyloxycarbonylmethyl)-α-D-glucopyranoside 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 methyl 4,6-O-benzylidene-2,3-di-O-(p-toluenesulfonyloxyethyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Carbohydrate-based aza-macrocycles by Richman-Atkins cyclization of glucopyranose precursors

  摘要：

  2, 3-Di-omega-halo-as well as 2, 3-di-omega-toluenesulfonamide-alkylated glucopyranoside derivatives were prepared. Their condensation with alpha,omega-bis-toluenesulfonamide components under varying Richman Atkins conditions with alkali carbonate in DMF led to carbohydrate-linked aza-macrocycles displaying 14-, 17-, 18-, 21-, 24-, and 25-membered ring structures. Isomeric aza-macrocylic coronands of 20-as well as 30-membered ring size containing two saccharides could be obtained employing Richman-Atkins condensations of two functionalized sugar building units. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2016.11.016