1-((4aR,6S,8aS)-2,2-Dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethane-1,2-diol | 143087-29-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((4aR,6S,8aS)-2,2-Dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethane-1,2-diol
• CAS: 143087-29-0
• 化学式: C₁₁H₂₀O₅
• 分子量: 232.277
• InChiKey: ONJLSVQLSJQCNR-JVSARINNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.04
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-((4aR,6S,8aS)-2,2-Dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethane-1,2-diol 在 sodium periodate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 12.5h， 生成 (4aR,8aS)-2,2-Dimethyl-6-<(E)-(tert-butyldimethylsiloxy)methylidene>pyrano<2,3-d>-1,3-dioxin
  参考文献：
  名称：

  Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

  摘要：

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.

  DOI：

  10.1021/jo00089a034
• 作为产物：
  描述：

  (4aR,8aS)-6-Benzenesulfonyl-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine 在 四氧化锇 、 N-甲基吲哚酮 、 zinc dibromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.0h， 生成 1-((4aR,6S,8aS)-2,2-Dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethane-1,2-diol
  参考文献：
  名称：

  针对微藻聚醚毒素的模型研究。2-苯基-磺酰基环状醚在制备反式，顺式，反式α-烷基，β-羟基取代的四氢吡喃亚基中的用途

  摘要：

  通过使用2-邻苯二甲酰基磺酰基中间体，从乙酸葡糖醛中合成了具有合适官能度的光学活性C 7-和C 8-四氢吡喃基亚基，用于进一步加工输注的聚醚毒素。通过应用该方法制备了双环反式，顺式，反式，氧杂环戊烷-氧杂戊基亚结构26。

  DOI：

  10.1016/s0040-4039(00)92095-1