(3aR,4aS,5R,6S,8aR,8bR)-5-azido-octahydro-2,2-dimethyl-4aH-benzofuro[2,3-d][1,3]dioxol-6-ol | 896441-57-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (3aR,4aS,5R,6S,8aR,8bR)-5-azido-octahydro-2,2-dimethyl-4aH-benzofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 896441-57-9
• 化学式: C₁₁H₁₇N₃O₄
• 分子量: 255.274
• InChiKey: TTXHNBJEUIPLOT-WHSUVHHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3aR,4aS,5R,6S,8aR,8bR)-5-azido-octahydro-2,2-dimethyl-4aH-benzofuro[2,3-d][1,3]dioxol-6-ol 在 sodium tetrahydroborate 、 戴斯-马丁氧化剂 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (3aR,4aS,5R,8aR,8bR)-5-azido-hexahydro-2,2-dimethyl-4aH-benzofuro[2,3-d][1,3]dioxol-6-ol
  参考文献：
  名称：

  Total synthesis of malayamycin A and analogues

  摘要：

  The total synthesis of the bicyclic C-nucleoside malayamycin A is described starting with D-ribonolactone. A new method was developed to obtain preparatively important quantities of beta-pseudouridine, which was used as an intermediate. The synthesis of a carba N-nucleoside analogue of malayamycin A is also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.066
• 作为产物：
  描述：

  在 sodium hydroxide 、 sodium azide 作用下， 以 四氢呋喃 、 乙二醇甲醚 、 水 为溶剂， 反应 3.0h， 生成 (3aR,4aS,5R,6S,8aR,8bR)-5-azido-octahydro-2,2-dimethyl-4aH-benzofuro[2,3-d][1,3]dioxol-6-ol
  参考文献：
  名称：

  Total synthesis of malayamycin A and analogues

  摘要：

  The total synthesis of the bicyclic C-nucleoside malayamycin A is described starting with D-ribonolactone. A new method was developed to obtain preparatively important quantities of beta-pseudouridine, which was used as an intermediate. The synthesis of a carba N-nucleoside analogue of malayamycin A is also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.066