9-decen-1-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 188428-15-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 9-decen-1-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS: 188428-15-1
• 化学式: C₂₄H₃₈O₁₀
• 分子量: 486.56
• InChiKey: JQODBDZWOUIDCV-GNADVCDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  34.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  9-decen-1-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 magnesium oxide 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 152.0h， 生成 9,10-epoxydecyl 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：

  9-十烯-1-醇 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 mercury dibromide 作用下， 以 二氯甲烷 为溶剂， 以29.9%的产率得到9-decen-1-yl 3,4,6-tri-O-acetyl-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