(+/-)-(1,3/2,4)-2,3-Di-O-acetyl-1,4-di-O-(2-hydroxyethyl)-5-cyclohexene-1,2,3,4-tetrol | 146288-32-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-(1,3/2,4)-2,3-Di-O-acetyl-1,4-di-O-(2-hydroxyethyl)-5-cyclohexene-1,2,3,4-tetrol
• CAS: 146288-32-6
• 化学式: C₁₄H₂₂O₈
• 分子量: 318.324
• InChiKey: HMKRQNGMYFRLTA-IGQOVBAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  111.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(1,3/2,4)-2,3-Di-O-acetyl-1,4-di-O-(2-hydroxyethyl)-5-cyclohexene-1,2,3,4-tetrol 在 2,4,6-三甲基吡啶 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 正丁胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (+/-)-(1,3/2,4)-1,4-Di-O-<2-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)ethyl>-5-cyclohexene-1,2,3,4-tetrol
  参考文献：
  名称：

  A spacer-modified disaccharide as a photoaffinity reagent for the acceptor-binding area of bovine (1 → 4)-β-d-galactosyltransferase: comparison of its acceptor properties with those of other 2-acetamido-2-deoxy-β-d-glucopyranosides

  摘要：

  The spacer-modified disaccharide 1,10-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-azi-1,10-decanediol (10) that mimics the biantennary. core heptasaccharide of N-glycoproteins has been synthesised. Compound 10 is an excellent acceptor in galactosyltransferase-catalysed galactosylation by UDP-galactose, is superior (7-8-fold) to analogues that have only one GlcNAc unit, and is an efficient photoaffinity reagent for galactosyltransferase. In the presence of UDP-Gal. no photoaffinity labelling by 10 takes place, which agrees the mechanism of galactosyltransferase action.

  DOI：

  10.1016/s0008-6215(00)90925-x
• 作为产物：
  描述：

  (1R,2R,3R,4R)-anti-benzene dioxide 在 吡啶 、 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 6.75h， 生成 (+/-)-(1,3/2,4)-2,3-Di-O-acetyl-1,4-di-O-(2-hydroxyethyl)-5-cyclohexene-1,2,3,4-tetrol
  参考文献：
  名称：

  A spacer-modified disaccharide as a photoaffinity reagent for the acceptor-binding area of bovine (1 → 4)-β-d-galactosyltransferase: comparison of its acceptor properties with those of other 2-acetamido-2-deoxy-β-d-glucopyranosides

  摘要：

  The spacer-modified disaccharide 1,10-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-azi-1,10-decanediol (10) that mimics the biantennary. core heptasaccharide of N-glycoproteins has been synthesised. Compound 10 is an excellent acceptor in galactosyltransferase-catalysed galactosylation by UDP-galactose, is superior (7-8-fold) to analogues that have only one GlcNAc unit, and is an efficient photoaffinity reagent for galactosyltransferase. In the presence of UDP-Gal. no photoaffinity labelling by 10 takes place, which agrees the mechanism of galactosyltransferase action.

  DOI：

  10.1016/s0008-6215(00)90925-x