(4aR,8aS)-4,4a,8,8a-Tetrahydro-6-<(benzyloxy)methyl>-2,2-dimethylpyrano<2,3-d>-1,3-dioxin | 159293-15-9

• 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: (4aR,8aS)-4,4a,8,8a-Tetrahydro-6-<(benzyloxy)methyl>-2,2-dimethylpyrano<2,3-d>-1,3-dioxin
• CAS: 159293-15-9
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: SGZVBCMUQLNASZ-JKSUJKDBSA-N

物化性质

• 沸点：
  391.3±42.0 °C(predicted)
• 密度：
  1.091±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4aR,8aS)-4,4a,8,8a-Tetrahydro-6-<(benzyloxy)methyl>-2,2-dimethylpyrano<2,3-d>-1,3-dioxin 在 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 作用下， 生成 2,6-Anhydro-7-O-benzyl-4-deoxy-1,3-O-isopropylidene-D-manno-heptitol 、 2,6-Anhydro-1-O-benzyl-4-deoxy-5,7-O-isopropylidene-D-allo-heptitol
  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
• 作为产物：
  描述：

  (4aR,8aS)-4,4a,8,8a-Tetrahydro-2,2-dimethyl-6-formylpyrano<2,3-d>-1,3-dioxin 在 四丁基溴化铵 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 3.5h， 生成 (4aR,8aS)-4,4a,8,8a-Tetrahydro-6-<(benzyloxy)methyl>-2,2-dimethylpyrano<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