(1S,2S)-1,2-bis[(2S)-oxiran-2-yl]ethane-1,2-diol | 132957-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S)-1,2-bis[(2S)-oxiran-2-yl]ethane-1,2-diol
• CAS: 132957-76-7
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: AAFJXZWCNVJTMK-UNTFVMJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  65.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1,2-bis[(2S)-oxiran-2-yl]ethane-1,2-diol 在 甲酸铵 作用下， 反应 2.0h， 以22%的产率得到2,5-脱水-D-葡萄糖醇
  参考文献：
  名称：

  Simple and efficient synthesis of 2,5-anhydro-d-glucitol

  摘要：

  The synthesis of 2,5-anhydro-D-glucitol is described via intramolecular cyclization of diepoxide using ammonium formate in MeOH by a microwave-assisted reaction. The overall yield was 32% from D-mannitol derivative involving seven steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.062
• 作为产物：
  描述：

  1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol 反应 0.17h， 以78%的产率得到(1S,2S)-1,2-bis[(2S)-oxiran-2-yl]ethane-1,2-diol
  参考文献：
  名称：

  Simple and efficient synthesis of 2,5-anhydro-d-glucitol

  摘要：

  The synthesis of 2,5-anhydro-D-glucitol is described via intramolecular cyclization of diepoxide using ammonium formate in MeOH by a microwave-assisted reaction. The overall yield was 32% from D-mannitol derivative involving seven steps. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.062

文献信息

• An enantio- and stereo-controlled synthesis of<scp>L</scp>-erythro- and<scp>D</scp>-threo-C₁₈-sphingosines via the anomalous version of the katsuki–sharpless asymmetric epoxidation reaction
  作者：Seiichi Takano、Yoshiharu Iwabuchi、Kunio Ogasawara

  DOI：10.1039/c39910000820

  日期：——

  A new enantiocontrolled synthesis of L-erythro- and D-threo-sphingosines has been established starting from (R,R)- and meso-1,2-divinylethylene glycols via the anomalous version of the Katsuki–Sharpless asymmetric epoxidation reaction as the key step.

  通过以Katsuki-Sharpless不对称环氧化反应的异常版本作为关键步骤，从(R,R)-和内消旋-1,2-二乙烯基乙二醇出发，已经建立了L-赤型和D-苏型的神经酰胺的新颖对映选择性合成方法。
• Inversion of enantioselectivity in the kinetic resolution mode of the Katsuki-Sharpless asymmetric epoxidation reaction
  作者：Seiichi Takano、Yoshiharu Iwabuchi、Kunio Ogasawara

  DOI：10.1021/ja00007a082

  日期：1991.3
• US7473757B2
  申请人：——

  公开号：US7473757B2

  公开（公告）日：2009-01-06
• Simple and efficient synthesis of 2,5-anhydro-d-glucitol
  作者：Valquiria Aragão-Leoneti、Ivone Carvalho

  DOI：10.1016/j.tetlet.2012.12.062

  日期：2013.2

  The synthesis of 2,5-anhydro-D-glucitol is described via intramolecular cyclization of diepoxide using ammonium formate in MeOH by a microwave-assisted reaction. The overall yield was 32% from D-mannitol derivative involving seven steps. (C) 2012 Elsevier Ltd. All rights reserved.