2,3'-脱水蔗糖 | 131158-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 中文名称: 2,3'-脱水蔗糖
• 英文名称: 2,3'-anhydrosucrose
• 英文别名: (1R,3S,5R,6R,7S,9R,10S,11S,12R)-3,5,12-tris(hydroxymethyl)-2,4,8,13-tetraoxatricyclo[7.4.0.03,7]tridecane-6,10,11-triol
• CAS: 131158-06-0
• 化学式: C₁₂H₂₀O₁₀
• 分子量: 324.285
• InChiKey: GLEFGUONDOLGII-UGDNZRGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3'-脱水蔗糖 在 吡啶 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 129.0h， 生成 3,6,1',4',6'-penta-O-acetyl-2,3'-anhydro-4-O-tosylsucrose
  参考文献：
  名称：

  2,3′-anhydrosucrose

  摘要：

  Alkaline hydrolysis of alpha-D-glucopyranosyl 3,4-anhydro-beta-D-ribo-hexulofuranoside (1) involves participation of HO-2 and leads to 2,3'-anhydrosucrose (2). The structure of 2 was assigned on the basis of the n.m.r. and mass spectra of its hexa-acetate 3 and confirmed by the formation from 2 of the 6,6'-di-(4) and 6,1',6'-tri-O-trityl (5) derivatives, the 4,6-O-isopropylidene derivative (6), and 2,3':3,4-dianhydro-galacto-sucrose, isolated as the tetra-acetate 7. The structure of 7 was confirmed by its conversion into the 4'-O-tosyl-6,1',6'-O-trityl derivative 14 and by unambiguous synthesis from 6.

  DOI：

  10.1016/0008-6215(90)80136-q
• 作为产物：
  描述：

  α-D-glucopyranosyl 3,4-anhydro-β-D-ribo-hexulofuranoside 在 sodium hydroxide 作用下， 反应 20.0h， 以74.9%的产率得到2,3'-脱水蔗糖
  参考文献：
  名称：

  2,3′-anhydrosucrose

  摘要：

  Alkaline hydrolysis of alpha-D-glucopyranosyl 3,4-anhydro-beta-D-ribo-hexulofuranoside (1) involves participation of HO-2 and leads to 2,3'-anhydrosucrose (2). The structure of 2 was assigned on the basis of the n.m.r. and mass spectra of its hexa-acetate 3 and confirmed by the formation from 2 of the 6,6'-di-(4) and 6,1',6'-tri-O-trityl (5) derivatives, the 4,6-O-isopropylidene derivative (6), and 2,3':3,4-dianhydro-galacto-sucrose, isolated as the tetra-acetate 7. The structure of 7 was confirmed by its conversion into the 4'-O-tosyl-6,1',6'-O-trityl derivative 14 and by unambiguous synthesis from 6.

  DOI：

  10.1016/0008-6215(90)80136-q

文献信息

• CAPEK, KAREL;CADOVA, EVA;SEDMERA, PETR, CARBOHYDR. RES., 205,(1990) C. 161-171
  作者：CAPEK, KAREL、CADOVA, EVA、SEDMERA, PETR

  DOI：——

  日期：——