methyl 3-O-dodecyl-β-D-glucopyranoside | 684230-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-dodecyl-β-D-glucopyranoside
• CAS: 684230-13-5
• 化学式: C₁₉H₃₈O₆
• 分子量: 362.507
• InChiKey: ZYEVQZHARWPXBU-IEWDOMPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  25.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.38
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 3-O-dodecyl-β-D-glucopyranoside 在 吡啶 作用下， 反应 18.0h， 以46%的产率得到methyl 2,4,6-tri-O-acetyl-3-O-dodecyl-β-D-glucopyranoside
  参考文献：
  名称：

  Organofluorine compounds and fluorinating agents

  摘要：

  Starting with 1,2,4,6-tetra-O-acetyl-3-O-dodecyl-beta-D-glucose (1), mixed alkyl-perfluoroalkyl substituted sugar derivatives with an anomeric perfluoroalkylthio group and an O-alkyl group in the 3 position were synthesized via 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-beta-D-glucose (4). The latter was S-perfluorohexylated with 1-iodoperfluorohexane in a dithionite initiated reaction yielding perfluorohexyl 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-beta-D-glucopyranoside (5). Experiments with the aim compound 5 completely to deacetylate ended in surprising results. Thus, methanolic methanolate solution produced the orthoester 7 as the result of a-fluoride replacement by methoxy groups as well as the methyl glucoside 8 as the result of a transglycosylation reaction. Alumina supported cesium fluoride cleaved regioselectively the two acetyl groups in the 4- and 6-position yielding perfluorohexyl 2-O-acetyl-3-O-dodecyl-1-thio-beta-D-glucopyranoside (10). A complete deacetylation of 5 to amphiphile 11 succeeded only with methanolic tert-butanolate. However, the products 8 and 10 were likewise formed. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2003.11.006
• 作为产物：
  描述：

  2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-β-D-glucopyranose 在 sodium dithionite 、 potassium tert-butylate 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 methyl 3-O-dodecyl-β-D-glucopyranoside
  参考文献：
  名称：

  Organofluorine compounds and fluorinating agents

  摘要：

  Starting with 1,2,4,6-tetra-O-acetyl-3-O-dodecyl-beta-D-glucose (1), mixed alkyl-perfluoroalkyl substituted sugar derivatives with an anomeric perfluoroalkylthio group and an O-alkyl group in the 3 position were synthesized via 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-beta-D-glucose (4). The latter was S-perfluorohexylated with 1-iodoperfluorohexane in a dithionite initiated reaction yielding perfluorohexyl 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-beta-D-glucopyranoside (5). Experiments with the aim compound 5 completely to deacetylate ended in surprising results. Thus, methanolic methanolate solution produced the orthoester 7 as the result of a-fluoride replacement by methoxy groups as well as the methyl glucoside 8 as the result of a transglycosylation reaction. Alumina supported cesium fluoride cleaved regioselectively the two acetyl groups in the 4- and 6-position yielding perfluorohexyl 2-O-acetyl-3-O-dodecyl-1-thio-beta-D-glucopyranoside (10). A complete deacetylation of 5 to amphiphile 11 succeeded only with methanolic tert-butanolate. However, the products 8 and 10 were likewise formed. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2003.11.006