(+/-)-1,6-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-psicose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-1,6-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-psicose
• 英文别名: (3S,4S,5S)-1,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3,4,5-trihydroxyhexan-2-one
• 化学式: C₁₈H₄₀O₆Si₂
• 分子量: 408.683
• InChiKey: GDINVFOWPVBWJX-CWRNSKLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.68
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+/-)-1,6-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-psicose 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 16.0h， 以100%的产率得到D-阿洛酮糖
  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：

  tert-butyl[(3S,6R)-6-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-3,6-dihydro-1,2-dioxin-3-yl]methoxydimethylsilane 在 salcomine 甲基磺酰胺 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 120.0h， 生成 (+/-)-1,6-bis-O-[(1,1-dimethylethyl)dimethylsilyl]-psicose
  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.