(3aR,5S,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole | 866890-76-8

• 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: (3aR,5S,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
• CAS: 866890-76-8
• 化学式: C₁₇H₂₂BrIO₆
• 分子量: 529.167
• InChiKey: URCHHVHUWGCEGM-QKPAOTATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aR,5S,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以72%的产率得到(3aR,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-2,2-dimethyl-5-methylene-tetrahydro-furo[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Radical cyclization of exo-methylene furanose derivatives: an expedient approach to the synthesis of chiral tricyclic nucleosides and benzannulated oxepine derivatives

  摘要：

  Tributyltin radical mediated cyclization of the glucose derived exo-methylene furanose derivatives 5a-c led to the highly functionalized cis-fused bicyclic ethers 6a-c. The product could subsequently be transformed to the optically active tricyclic nucleoside analogue 8 or oxepine derivative 9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.054
• 作为产物：
  描述：

  在 咪唑 、 sodium tetrahydroborate 、 sodium periodate 、 碘 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 水 、 苯 为溶剂， 反应 6.0h， 生成 (3aR,5S,6R,6aR)-6-(2-bromo-4,5-dimethoxy-benzyloxy)-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Radical cyclization of exo-methylene furanose derivatives: an expedient approach to the synthesis of chiral tricyclic nucleosides and benzannulated oxepine derivatives

  摘要：

  Tributyltin radical mediated cyclization of the glucose derived exo-methylene furanose derivatives 5a-c led to the highly functionalized cis-fused bicyclic ethers 6a-c. The product could subsequently be transformed to the optically active tricyclic nucleoside analogue 8 or oxepine derivative 9. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.07.054