6-O-octanoyl-1,2-O-cyclohexylidene-α-D-glucofuranose

• 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: 6-O-octanoyl-1,2-O-cyclohexylidene-α-D-glucofuranose
• 英文别名: [(2R)-2-[(3aR,5R,6S,6aR)-6-hydroxyspiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-5-yl]-2-hydroxyethyl] octanoate
• 化学式: C₂₀H₃₄O₇
• 分子量: 386.486
• InChiKey: YZIGYFNFFQROQK-RSRPTUBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-O-octanoyl-1,2-O-cyclohexylidene-α-D-glucofuranose 在 水 、 三氟乙酸 作用下， 反应 1.5h， 以69%的产率得到6-O-capryloyl-D-glucopyranose
  参考文献：
  名称：

  Chemoenzymatic synthesis of glucose fatty esters

  摘要：

  D-Glucose fatty esters at C-6 were obtained by chemoenzymatic synthesis involving 1,2-O-cyclohexylidene-alpha-D-glucofuranose (1) followed by hydrolysis of the cyclohexylidene protecting group. The enzymatic esterification of 1 was performed with fatty acids of variable chain lengths (C8:0 to C18:0). The kinetic of the reaction was studied for each fatty acid and the structure of the octanoyl ester was determined by H-1 and C-13 NMR spectroscopy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00340-0
• 作为产物：
  描述：

  1,2-O-亚环己基-Alpha-D-呋喃葡萄糖 、 辛酸 在 lipozyme 作用下， 60.0 ℃ 、21.33 kPa 条件下， 反应 8.0h， 以75%的产率得到6-O-octanoyl-1,2-O-cyclohexylidene-α-D-glucofuranose
  参考文献：
  名称：

  Chemoenzymatic synthesis of glucose fatty esters

  摘要：

  D-Glucose fatty esters at C-6 were obtained by chemoenzymatic synthesis involving 1,2-O-cyclohexylidene-alpha-D-glucofuranose (1) followed by hydrolysis of the cyclohexylidene protecting group. The enzymatic esterification of 1 was performed with fatty acids of variable chain lengths (C8:0 to C18:0). The kinetic of the reaction was studied for each fatty acid and the structure of the octanoyl ester was determined by H-1 and C-13 NMR spectroscopy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00340-0

文献信息

• Chemoenzymatic synthesis of glucose fatty esters
  作者：Ines Redmann、Michel Pina、Bernard Guyot、Pierre Blaise、Marie Farines、Jean Graille

  DOI：10.1016/s0008-6215(96)00340-0

  日期：1997.5

  D-Glucose fatty esters at C-6 were obtained by chemoenzymatic synthesis involving 1,2-O-cyclohexylidene-alpha-D-glucofuranose (1) followed by hydrolysis of the cyclohexylidene protecting group. The enzymatic esterification of 1 was performed with fatty acids of variable chain lengths (C8:0 to C18:0). The kinetic of the reaction was studied for each fatty acid and the structure of the octanoyl ester was determined by H-1 and C-13 NMR spectroscopy. (C) 1997 Elsevier Science Ltd.