perfluorohexyl 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-β-D-glucopyranoside | 684230-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: perfluorohexyl 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,5-diacetyloxy-4-dodecoxy-6-(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 684230-10-2
• 化学式: C₃₀H₄₁F₁₃O₈S
• 分子量: 808.696
• InChiKey: VANVSAHRSBUSIL-SJSRKZJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  52
• 可旋转键数：
  25
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  perfluorohexyl 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-β-D-glucopyranoside 在 吡啶 、 sodium methylate 作用下， 反应 19.0h， 生成 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：

  Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-2-carbamimidoylsulfanyl-4-dodecyloxy-tetrahydro-pyran-3-yl ester; hydrobromide 在 sodium metabisulfite 、 sodium dithionite 、 碳酸氢钠 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.17h， 生成 perfluorohexyl 2,4,6-tri-O-acetyl-3-O-dodecyl-1-thio-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