[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(8-hydroxyoctoxy)oxan-2-yl]methyl acetate | 188778-83-8

• 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)-3,4,5-triacetyloxy-6-(8-hydroxyoctoxy)oxan-2-yl]methyl acetate
• CAS: 188778-83-8
• 化学式: C₂₂H₃₆O₁₁
• 分子量: 476.521
• InChiKey: NCGDJONCNCUEQX-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(8-hydroxyoctoxy)oxan-2-yl]methyl acetate 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 26.92h， 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：

  (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((8-acetoxyoctyl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 lipase Amano P 作用下， 以 异丙醚 、 水 为溶剂， 反应 22.0h， 以80%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(8-hydroxyoctoxy)oxan-2-yl]methyl acetate
  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

文献信息

• De Groot; Vanden Bempt; Bormans, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S520-S521
  作者：De Groot、Vanden Bempt、Bormans、Koepsell、Mortelmans、Verbruggen

  DOI：——

  日期：——