Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-bromo-4-dodecyloxy-tetrahydro-pyran-3-yl ester | 147315-41-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-bromo-4-dodecyloxy-tetrahydro-pyran-3-yl ester
• CAS: 147315-41-1
• 化学式: C₂₄H₄₁BrO₈
• 分子量: 537.489
• InChiKey: LUMAJJKTAFNYIB-SJSRKZJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  33.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-bromo-4-dodecyloxy-tetrahydro-pyran-3-yl ester 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 、 丙酮 为溶剂， 反应 3.92h， 生成 bis-(2,4,6-tri-O-acetyl-3-O-dodecyl-β-D-glucopyranosyl)disulfide
  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：

  1,2,4,6-tetra-O-acetyl-3-O-dodecyl-β-D-glucopyranose 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 1.5h， 生成 Acetic acid (2R,3R,4S,5R,6R)-5-acetoxy-2-acetoxymethyl-6-bromo-4-dodecyloxy-tetrahydro-pyran-3-yl ester
  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