(-)-1,2:5,6-Di-O-isopropylidene-3-O-(ethoxycarbonyl)methyl-α-D-glucofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-1,2:5,6-Di-O-isopropylidene-3-O-(ethoxycarbonyl)methyl-α-D-glucofuranose
• 英文别名: ethyl 2-[[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]acetate
• 化学式: C₁₆H₂₆O₈
• 分子量: 346.378
• InChiKey: TYKKLZVUSKDBFG-IBYNPJLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (-)-1,2:5,6-Di-O-isopropylidene-3-O-(ethoxycarbonyl)methyl-α-D-glucofuranose 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 [(3aR,5R,6S,6aR)-5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester
  参考文献：
  名称：

  Chikashita, Hidenori; Ouchi, Tatsuro, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 981 - 983

  摘要：

  DOI：
• 作为产物：
  描述：

  重氮乙酸乙酯 、 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 indium(III) chloride 作用下， 反应 4.0h， 以72%的产率得到(-)-1,2:5,6-Di-O-isopropylidene-3-O-(ethoxycarbonyl)methyl-α-D-glucofuranose
  参考文献：
  名称：

  InCl3 catalyzed carbene insertion into O–H bonds: efficient synthesis of ethers

  摘要：

  An efficient InCl3 mediated insertion of the carbene fragment (:CHCO2Et), generated in situ from ethyl diazoacetate into O-H bond of a series of saturated and unsaturated alcohols under mild conditions has been developed to afford the corresponding ethers as exclusive products in good to high yields (70-95%) and in shorter reaction times. In the case of unsaturated alcohols, the reaction proceeded with unprecedented selectivity resulting in ethers as the only products and in high yields. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.099

文献信息

• InCl3 catalyzed carbene insertion into O–H bonds: efficient synthesis of ethers
  作者：Palakodety Radha Krishna、Y. Lakshmi Prapurna、Munagala Alivelu

  DOI：10.1016/j.tetlet.2011.04.099

  日期：2011.7

  An efficient InCl3 mediated insertion of the carbene fragment (:CHCO2Et), generated in situ from ethyl diazoacetate into O-H bond of a series of saturated and unsaturated alcohols under mild conditions has been developed to afford the corresponding ethers as exclusive products in good to high yields (70-95%) and in shorter reaction times. In the case of unsaturated alcohols, the reaction proceeded with unprecedented selectivity resulting in ethers as the only products and in high yields. (C) 2011 Elsevier Ltd. All rights reserved.
• Chikashita, Hidenori; Ouchi, Tatsuro, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 981 - 983
  作者：Chikashita, Hidenori、Ouchi, Tatsuro

  DOI：——

  日期：——