1,4-dideoxy-scyllo-inositol | 1068088-21-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-dideoxy-scyllo-inositol
• 英文别名: 1r,2t,4t,5c-Tetrahydroxy-cyclohexan；cyclohexanetetrol-(1r,2t,4t,5c)；Cyclohexantetrol-(1r,2t,4t,5c)；(1R,2R,4S,5S)-cyclohexane-1,2,4,5-tetrol
• CAS: 1068088-21-0
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: RDIDGZFQASQXBU-FBXFSONDSA-N

物化性质

• 沸点：
  297.1±40.0 °C(predicted)
• 密度：
  1.569±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 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：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-dideoxy-scyllo-inositol 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以275 mg的产率得到trans,trans-(1RS,2RS,4SR,5SR)-cyclohexane-1,2,4,5-tetrayl tetraacetate
  参考文献：
  名称：

  Ring opening of epoxides with NaHSO4: isolation of β-hydroxy sulfate esters and an effective synthesis for trans-diols

  摘要：

  Sodium hydrogen sulfate (NaHSO4) was observed to be highly effective as a reagent or catalyst in the ring-opening reactions of epoxides under mild conditions. Reaction of epoxides with NaHSO4 gave isolable P-hydroxy sulfate esters and vicinal diols. Experimenting with different epoxides, the study investigated the scope of the ring-opening reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.092
• 作为产物：
  描述：

  (1S,3S,5R,7R)-4,8-dioxa-tricyclo[5.1.0.0]octane 在 sodium hydrogen sulfate 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 1,4-dideoxy-scyllo-inositol
  参考文献：
  名称：

  Ring opening of epoxides with NaHSO4: isolation of β-hydroxy sulfate esters and an effective synthesis for trans-diols

  摘要：

  Sodium hydrogen sulfate (NaHSO4) was observed to be highly effective as a reagent or catalyst in the ring-opening reactions of epoxides under mild conditions. Reaction of epoxides with NaHSO4 gave isolable P-hydroxy sulfate esters and vicinal diols. Experimenting with different epoxides, the study investigated the scope of the ring-opening reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.092

文献信息

• Synthesis of scyllo-inositol derivatives and their effects on amyloid beta peptide aggregation
  作者：Yedi Sun、Guohua Zhang、Cheryl A. Hawkes、James E. Shaw、JoAnne McLaurin、Mark Nitz

  DOI：10.1016/j.bmc.2008.06.045

  日期：2008.8

  scyllo-inositol derivatives have been synthesized which contain deoxy, fluoro, chloro, and methoxy substitutions. The effects of these compounds on the aggregation cascade of Abeta42 have been investigated using electron microscopy (EM). EM analyses revealed that the 1-deoxy-1-fluoro- and 1,4-dimethyl-scyllo-inositols significantly inhibit the formation of Abeta42 fibers. The other derivatives showed some alterations

  scyllo-肌醇通过与淀粉样蛋白β（Abeta）肽直接相互作用抑制Abeta42纤维形成，已显示出有望作为阿尔茨海默氏病的潜在治疗剂。为了探索肌醇-Abeta42相互作用的分子细节，已合成了一系列含有脱氧，氟，氯和甲氧基取代的鞘氨醇衍生物。这些化合物对Abeta42的聚集级联反应的影响已使用电子显微镜（EM）进行了研究。EM分析表明，1-脱氧-1-氟-和1,4-二甲基-scyllo-肌醇显着抑制Abeta42纤维的形成。其他衍生物在生产的Abeta42纤维的形态上显示出一些变化。