5,6-diacetoxyhexyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside | 188428-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-diacetoxyhexyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside
• CAS: 188428-43-5
• 化学式: C₂₃H₃₆O₁₃
• 分子量: 520.531
• InChiKey: YLYVABKDECHZFK-QGFPMTTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  36.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  159.19
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  5,6-diacetoxyhexyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以79%的产率得到5,6-dihydroxyhexyl 3-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of spacer-armed carbohydrate model compounds

  摘要：

  Commercially available chemicals, such as diethylene glycol, 1,9-nonanediol, 9-decen-1-ol, 1,2,6-hexanetriol, and p-nitrophenol were used to prepare spacer-armed carbohydrate derivatives. Glycosides of D-glucose, N-acetyl-D-glucosamine and 3-O-methyl-D-glucose have been synthesized, carrying reactive groups at the end of the spacer-arms. These glycosides are capable of forming neoglycoproteins. When bromo sugars were reacted with highly apolar aglycones in the presence of mercuric cyanide or mercuric bromide, a considerable amount of '2-OH-compounds' (such as 9-hydroxynonyl 3,4,6-tri-O-acetyl-beta-D-glucopyranoside) were formed. Some spacer-armed derivatives (such as 9,10-epoxydecyl beta-D-glucopyranoside) are theoretically a mixture of diastereomers, but this fact does not mirror in the H-1 and C-13 NMR spectra. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00256-x
• 作为产物：
  描述：

  1,2,6-己三醇 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 氢气 、 对甲苯磺酸 、 溶剂黄146 、 mercury dibromide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 5,6-diacetoxyhexyl 2,4,6-tri-O-acetyl-3-O-methyl-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of spacer-armed carbohydrate model compounds

  摘要：

  Commercially available chemicals, such as diethylene glycol, 1,9-nonanediol, 9-decen-1-ol, 1,2,6-hexanetriol, and p-nitrophenol were used to prepare spacer-armed carbohydrate derivatives. Glycosides of D-glucose, N-acetyl-D-glucosamine and 3-O-methyl-D-glucose have been synthesized, carrying reactive groups at the end of the spacer-arms. These glycosides are capable of forming neoglycoproteins. When bromo sugars were reacted with highly apolar aglycones in the presence of mercuric cyanide or mercuric bromide, a considerable amount of '2-OH-compounds' (such as 9-hydroxynonyl 3,4,6-tri-O-acetyl-beta-D-glucopyranoside) were formed. Some spacer-armed derivatives (such as 9,10-epoxydecyl beta-D-glucopyranoside) are theoretically a mixture of diastereomers, but this fact does not mirror in the H-1 and C-13 NMR spectra. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00256-x