(3R,4S,5R,6S)-3,6-dimethyl-1,2-dioxane-4,5-diol | 912362-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (3R,4S,5R,6S)-3,6-dimethyl-1,2-dioxane-4,5-diol
• 英文别名: (3S,4R,5S,6R)-3,6-dimethyldioxane-4,5-diol
• CAS: 912362-48-2
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: NEROCICURITUNM-FBXFSONDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,5R,6S)-3,6-dimethyl-1,2-dioxane-4,5-diol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以66%的产率得到1,6-dideoxyallitol
  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：

  cis-3,6-dimethyl-1,2-dioxa-4-cyclohexene 在 potassium osmate(VI) 、 N-甲基吲哚酮 、 柠檬酸 作用下， 以 水 为溶剂， 反应 24.0h， 以95%的产率得到(3R,4S,5R,6S)-3,6-dimethyl-1,2-dioxane-4,5-diol
  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

文献信息

• Osmium Catalyzed Dihydroxylation of 1,2-Dioxines:  A New Entry for Stereoselective Sugar Synthesis
  作者：Tony V. Robinson、Dennis K. Taylor、Edward R. T. Tiekink

  DOI：10.1021/jo060949p

  日期：2006.9.1

  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.