(3aR,4S,7R,7aS)-2,2-dimethyl-4,7-dipropylperhydro[1,3]-dioxolo[4,5-d][1,2]dioxine | 912362-64-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4S,7R,7aS)-2,2-dimethyl-4,7-dipropylperhydro[1,3]-dioxolo[4,5-d][1,2]dioxine
• 英文别名: (3aS,4R,7S,7aR)-2,2-dimethyl-4,7-dipropyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-d][1,2]dioxine
• CAS: 912362-64-2
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: ZDMGBDWKBCDNBS-BKUVIOGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,4S,7R,7aS)-2,2-dimethyl-4,7-dipropylperhydro[1,3]-dioxolo[4,5-d][1,2]dioxine 在 salcomine 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以100%的产率得到(+/-)-(3aS,6S,6aS)-2,2-dimethyl-4,6-dipropylperhydro[3,4-d][1,3]dioxol-4-ol
  参考文献：
  名称：

  Osmium Catalyzed Dihydroxylation of 1,2-Dioxines:  A New Entry for Stereoselective Sugar Synthesis

  摘要：

  A series of 3,6-substituted 3,6-dihydro-1,2-dioxines were dihydroxylated with osmium tetroxide to furnish 1,2-dioxane-4,5-diols (peroxy diols) in yields ranging from 33% to 98% and with de values not less than 90%. The peroxy diols were then reduced to generate a stereospecific tetraol core with R, R, S, S or "allitol" stereochemistry. The peroxy diols and their acetonide derivatives were also ring-opened with Co(II) salen complexes to give novel hydroxy ketones in 77-100% yield, including the natural sugar psicose. Importantly, preliminary work on the catalytic asymmetric ring-opening of meso-peroxy diols using the Co(II) Jacobsens's catalyst indicates that asymmetric sugar synthesis from 1,2-dioxines is possible.

  DOI：

  10.1021/jo060949p
• 作为产物：
  描述：

  3,6-dipropyl-3,6-dihydro-1,2-dioxine 在 potassium osmate(VI) 、 N-甲基吲哚酮 、 对甲苯磺酸 、 柠檬酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 (3aR,4S,7R,7aS)-2,2-dimethyl-4,7-dipropylperhydro[1,3]-dioxolo[4,5-d][1,2]dioxine
  参考文献：
  名称：

  Osmium Catalyzed Dihydroxylation of 1,2-Dioxines:  A New Entry for Stereoselective Sugar Synthesis

  摘要：

  A series of 3,6-substituted 3,6-dihydro-1,2-dioxines were dihydroxylated with osmium tetroxide to furnish 1,2-dioxane-4,5-diols (peroxy diols) in yields ranging from 33% to 98% and with de values not less than 90%. The peroxy diols were then reduced to generate a stereospecific tetraol core with R, R, S, S or "allitol" stereochemistry. The peroxy diols and their acetonide derivatives were also ring-opened with Co(II) salen complexes to give novel hydroxy ketones in 77-100% yield, including the natural sugar psicose. Importantly, preliminary work on the catalytic asymmetric ring-opening of meso-peroxy diols using the Co(II) Jacobsens's catalyst indicates that asymmetric sugar synthesis from 1,2-dioxines is possible.

  DOI：

  10.1021/jo060949p