(E)-(1,2;5,6-di-O-isopropyliden-α-D-glucofuranose-3-O-yl) 2-methyl-2-butenoate | 143994-00-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(1,2;5,6-di-O-isopropyliden-α-D-glucofuranose-3-O-yl) 2-methyl-2-butenoate
• CAS: 143994-00-7
• 化学式: C₁₇H₂₆O₇
• 分子量: 342.389
• InChiKey: YVAQQYZTDCYCAL-ZIIDSXHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (E)-(1,2;5,6-di-O-isopropyliden-α-D-glucofuranose-3-O-yl) 2-methyl-2-butenoate 在 N,N-二甲基乙醇胺 作用下， 以 正己烷 为溶剂， 以79%的产率得到(1,2;5,6-di-O-isopropyliden-α-D-glucofuranose-3-O-yl) 2-methyl-3-butenoate
  参考文献：
  名称：

  Diacetone D-glucose: Efficient chiral building block for asymmetric photodeconjugation

  摘要：

  Irradiation of alpha-substituted, alpha,beta-unsaturated esters of 1,2;5,6-di-O-isopropylidene-alpha-D-glucofuranose leads to the formation of beta,gamma-isomers with high d.e. (up to 98%) whatever the substitution of the chain. A very strong dependence of the nature of the protonating agent upon the selectivity and the configuration of the new chiral center is observed.

  DOI：

  10.1016/s0957-4166(00)80517-0
• 作为产物：
  描述：

  惕格酸 、 双丙酮葡萄糖 在 4-二甲氨基吡啶 、 4 A molecular sieve 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到(E)-(1,2;5,6-di-O-isopropyliden-α-D-glucofuranose-3-O-yl) 2-methyl-2-butenoate
  参考文献：
  名称：

  Diacetone D-glucose: Efficient chiral building block for asymmetric photodeconjugation

  摘要：

  Irradiation of alpha-substituted, alpha,beta-unsaturated esters of 1,2;5,6-di-O-isopropylidene-alpha-D-glucofuranose leads to the formation of beta,gamma-isomers with high d.e. (up to 98%) whatever the substitution of the chain. A very strong dependence of the nature of the protonating agent upon the selectivity and the configuration of the new chiral center is observed.

  DOI：

  10.1016/s0957-4166(00)80517-0

文献信息

• Diacetone D-glucose: Efficient chiral building block for asymmetric photodeconjugation
  作者：Olivier Piva、Jean-Pierre Pete

  DOI：10.1016/s0957-4166(00)80517-0

  日期：1992.6

  Irradiation of alpha-substituted, alpha,beta-unsaturated esters of 1,2;5,6-di-O-isopropylidene-alpha-D-glucofuranose leads to the formation of beta,gamma-isomers with high d.e. (up to 98%) whatever the substitution of the chain. A very strong dependence of the nature of the protonating agent upon the selectivity and the configuration of the new chiral center is observed.