(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((8-acetoxyoctyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 724771-76-0

• 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: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((8-acetoxyoctyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 724771-76-0
• 化学式: C₂₄H₃₈O₁₂
• 分子量: 518.559
• InChiKey: BYUICGFKIPEOEH-GNADVCDUSA-N

物化性质

• 沸点：
  554.8±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  36.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  149.96
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((8-acetoxyoctyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 lipase Amano P 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 异丙醚 、 水 、 二甲基亚砜 为溶剂， 反应 48.92h， 生成 octyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of rhodiooctanoside isolated from Chinese medicines, rhodiolae radix

  摘要：

  Direct beta-glucosidation between 1,8-octanediol 5 and D-glucose 6 using the immobilized beta-glucosidase (EC 3.2.1.21) from almonds with the synthetic prepolymer ENTP-4000 gave mono-beta-glucoside 3 in 58% yield, which was converted into n-octyl beta-D-glucopyranoside 2 by means of a chemoenzymatic method. The coupling of n-octyl beta-D-glucopyranoside congener 15 and 2,3,4-tri-O-acetyl-alpha-L-arabinopyranosyl bromide 17, followed by deprotection afforded the synthetic rhodiooctanoside 1, which was identical with natural 1 with respect to the spectral data and specific rotation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.046
• 作为产物：
  描述：

  乙酸酐 、 8-hydroxyoctyl β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 1.0h， 以100%的产率得到(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((8-acetoxyoctyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Chemoenzymatic synthesis of rhodiooctanoside isolated from Chinese medicines, rhodiolae radix

  摘要：

  Direct beta-glucosidation between 1,8-octanediol 5 and D-glucose 6 using the immobilized beta-glucosidase (EC 3.2.1.21) from almonds with the synthetic prepolymer ENTP-4000 gave mono-beta-glucoside 3 in 58% yield, which was converted into n-octyl beta-D-glucopyranoside 2 by means of a chemoenzymatic method. The coupling of n-octyl beta-D-glucopyranoside congener 15 and 2,3,4-tri-O-acetyl-alpha-L-arabinopyranosyl bromide 17, followed by deprotection afforded the synthetic rhodiooctanoside 1, which was identical with natural 1 with respect to the spectral data and specific rotation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.03.046