3,4-O-methylene-D-mannitol | 33471-15-7

• 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: 3,4-O-methylene-D-mannitol
• 英文别名: O²,O³-methanediyl-D-mannitol；O²,O³-Methandiyl-D-mannit；(1R)-1-[(4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-1,3-dioxolan-4-yl]ethane-1,2-diol
• CAS: 33471-15-7
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: QOAKSDZRDJHIFS-DBRKOABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4-O-methylene-D-mannitol 在 吡啶 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Catalytic and enantioselective bromoetherification of olefinic 1,3-diols: mechanistic insight

  摘要：

  How can high enantioselectivity be achieved when the racemic background reaction proceeds at a rate comparable to that of the catalytic asymmetric reaction? We attempted to rationalize this counterin-tuitive observation by studying the effect of (1) catalyst structure, (2) temperature and addition sequence of components, (3) catalyst loading, and (4) Bronsted acid additives. In the course of our investigation, it was found that increasing the amount of catalyst used led to inhibition of the stoichiometric reaction. Olefinic 1,3-diol 1, 5 mol % of catalyst 3a, 1 equiv of MsOH, and NBS were added at low temperature in a specific sequence to provide the best performance for the enantioselective bromoetherification. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.016
• 作为产物：
  描述：

  (4R)-4-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 3,4-O-methylene-D-mannitol
  参考文献：
  名称：

  Catalytic and enantioselective bromoetherification of olefinic 1,3-diols: mechanistic insight

  摘要：

  How can high enantioselectivity be achieved when the racemic background reaction proceeds at a rate comparable to that of the catalytic asymmetric reaction? We attempted to rationalize this counterin-tuitive observation by studying the effect of (1) catalyst structure, (2) temperature and addition sequence of components, (3) catalyst loading, and (4) Bronsted acid additives. In the course of our investigation, it was found that increasing the amount of catalyst used led to inhibition of the stoichiometric reaction. Olefinic 1,3-diol 1, 5 mol % of catalyst 3a, 1 equiv of MsOH, and NBS were added at low temperature in a specific sequence to provide the best performance for the enantioselective bromoetherification. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.016

文献信息

• Synthesis of C 2 -symmetric guanidino-sugars as potent inhibitors of glycosidases
  作者：Yves Le Merrer、Laurence Gauzy、Christine Gravier-Pelletier、Jean-Claude Depezay

  DOI：10.1016/s0968-0896(99)00294-1

  日期：2000.2

  A series of enantiomerically pure C-2-Symmetric guanidino-sugars was synthesized from D-mannitol. The first method described involves direct opening of a bis-epoxide by guanidine, whereas the second one deals with a mercury-catalyzed transformation of a cyclic thiourea into a N,N,N"-trisubstituted guanidine as a key step. The biological activity of these compounds towards several glycosidases has been evaluated. One of them (5) was found to selectively inhibit alpha-L-fucosidase of bovin kidney (2.8 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.
• New Methylene Derivatives of D-Mannitol and 1,4-Anhydro-D-mannitol
  作者：Hewitt G. Fletcher、Harry W. Diehl

  DOI：10.1021/ja01135a025

  日期：1952.8