(2R,4aR,6S,7S,9R,9aR)-6,7-Dimethoxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-e][1,4]dioxepin-9-ol | 137694-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: (2R,4aR,6S,7S,9R,9aR)-6,7-Dimethoxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-e][1,4]dioxepin-9-ol
• CAS: 137694-05-4
• 化学式: C₁₅H₂₀O₇
• 分子量: 312.32
• InChiKey: NKZSNFZBTVOKNQ-MBIARJLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.78
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,4aR,6S,7S,9R,9aR)-6,7-Dimethoxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-e][1,4]dioxepin-9-ol 在 oxonium 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (2R,4S,5R)-5-hydroxy-2-phenyl-4-vinyl-1,3-dioxane
  参考文献：
  名称：

  Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.

  摘要：

  Cleavage of glucosides with NalO4 in MeOH furnishes sesqui-acetals (protected dialdehydes). Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses). Proper choice of protecting groups can affect the face selectivity of the oxymercuration step to provide only the desired beta-C-anomer.

  DOI：

  10.1016/s0040-4039(00)93472-5
• 作为产物：
  描述：

  甲醇 、 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 在 sodium periodate 作用下， 以70%的产率得到(2R,4aR,6S,7S,9R,9aR)-6,7-Dimethoxy-2-phenyl-hexahydro-[1,3]dioxino[5,4-e][1,4]dioxepin-9-ol
  参考文献：
  名称：

  Erythrose sesqui-acetals as electrophiles. 2-Deoxy-C-nucleosides from D-glucose.

  摘要：

  Cleavage of glucosides with NalO4 in MeOH furnishes sesqui-acetals (protected dialdehydes). Olefination of these substrates, followed by endocyclic oxymercuration-demercuration furnishes substituted tetrahydrofurans (1,2-dideoxy-1-aryl-D-ribofuranoses). Proper choice of protecting groups can affect the face selectivity of the oxymercuration step to provide only the desired beta-C-anomer.

  DOI：

  10.1016/s0040-4039(00)93472-5