2-O-hydrocinnamoylsucrose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-hydrocinnamoylsucrose
• 英文别名: [(2R,3R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 3-phenylpropanoate
• 化学式: C₂₁H₃₀O₁₂
• 分子量: 474.462
• InChiKey: OZNVBYHDYVJHED-JTWLPENBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3-苯基-1-(2-硫代噻唑烷-3-基)丙烷-1-酮 、 蔗糖 在 吡啶 、 sodium hydride 作用下， 反应 3.0h， 以50%的产率得到2-O-hydrocinnamoylsucrose
  参考文献：
  名称：

  New highly regioselective reactions of unprotected sucrose. Synthesis of 2-O-acylsucroses and 2-O-(N-alkylcarbamoyl)sucroses

  摘要：

  New methodologies which lead selectively to chosen regioisomeric mono-O-acylsucroses are described. The results indicate that a selective ionization of the free sugar makes the secondary 2-OH group of the glucose moiety more nucleophilic than the primary hydroxyls. New 2-O-acylsucroses 2 and 2-O-(N-alkylcarbamoyl)sucroses 3 were thus obtained in high yields.

  DOI：

  10.1021/jo00060a053

文献信息

• New highly regioselective reactions of unprotected sucrose. Synthesis of 2-O-acylsucroses and 2-O-(N-alkylcarbamoyl)sucroses
  作者：Caroline Chauvin、Krystyna Baczko、Daniel Plusquellec

  DOI：10.1021/jo00060a053

  日期：1993.4

  New methodologies which lead selectively to chosen regioisomeric mono-O-acylsucroses are described. The results indicate that a selective ionization of the free sugar makes the secondary 2-OH group of the glucose moiety more nucleophilic than the primary hydroxyls. New 2-O-acylsucroses 2 and 2-O-(N-alkylcarbamoyl)sucroses 3 were thus obtained in high yields.