5-Hydroxypentyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 146289-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Hydroxypentyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 146289-33-0
• 化学式: C₂₅H₃₁NO₁₁
• 分子量: 521.521
• InChiKey: LGNDCLAHWKHMLN-ANOZEODCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  154.97
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5-Hydroxypentyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 正丁胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成
  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：

  2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 、 1,5-戊二醇 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到5-Hydroxypentyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  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