tert-butyl[(3S,6R)-6-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-3,6-dihydro-1,2-dioxin-3-yl]methoxydimethylsilane | 912362-41-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: tert-butyl[(3S,6R)-6-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-3,6-dihydro-1,2-dioxin-3-yl]methoxydimethylsilane
• 英文别名: tert-butyl-[[(3R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,6-dihydro-1,2-dioxin-3-yl]methoxy]-dimethylsilane
• CAS: 912362-41-5
• 化学式: C₁₈H₃₈O₄Si₂
• 分子量: 374.668
• InChiKey: FIKLKQPRUJFHNS-IYBDPMFKSA-N

物化性质

• 沸点：
  341.7±35.0 °C(Predicted)
• 密度：
  0.922±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  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 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 136.0h， 生成 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：

  (2E,4E)-1,6-Bis-(tert-butyl-dimethyl-silanyloxy)-hexa-2,4-diene 在 氧气 、 Rose Bengal bis(triethylammonium) salt 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以92%的产率得到tert-butyl[(3S,6R)-6-([1-(tert-butyl)-1,1-dimethylsilyl]oxymethyl)-3,6-dihydro-1,2-dioxin-3-yl]methoxydimethylsilane
  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.