[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-2-(decoxymethyl)-6-fluorooxan-3-yl] acetate | 138188-86-0

• 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: [(2R,3S,4S,5R,6R)-4,5-diacetyloxy-2-(decoxymethyl)-6-fluorooxan-3-yl] acetate
• CAS: 138188-86-0
• 化学式: C₂₂H₃₇FO₈
• 分子量: 448.529
• InChiKey: BTALDZIISLJQRB-CTWRKMMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6R)-4,5-diacetyloxy-2-(decoxymethyl)-6-fluorooxan-3-yl] acetate 在 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.5h， 以87.6%的产率得到(2R,3R,4S,5R,6R)-2-Decyloxymethyl-6-fluoro-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Organofluorine compounds and fluorinating agents. 14. Thermotropic Liquid-Crystalline Glycosyl Fluorides

  摘要：

  The liquid crystalline 6-O-alkyl-alpha-D-galactopyranosyl fluorides (3a-f) and the mesogenic 6-O-dodecyl-alpha-D-glucopyranosyl fluoride (7) were prepared from the homologous 6-O-alkyl-1,2:3,4-di-O-isopropylidene-alpha-D-galacto-pyranosides (1a-f) and from the methyl 2,3,4-tri-O-benzyl-glucopyranoside (4), respectively, in two and three steps. The fluorinations of 1a-f to the alpha-fluorides 2a-f and of 5 to the alpha-fluoride 6 were carried out with the reagent system HF/nitromethane/acetic anhydride, which simultaneously effects the complete exchange of the isopropylidene groups (1a-f) and of the benzyl groups (5) for acetyl functions in the non-glycosidic positions. Moreover, the 6-O-dodecyl-2,3,4-tri-O-acetyl-beta-D-galactopyranosyl fluoride (11) was prepared in three steps from the 6-O-dodecyl-galactopyranose (8). The stereoselective introduction of the fluoride into the beta-anomeric position (10 --> 11) was achieved by bromide-fluoride exchange with the two-phase system triethylamine-trishydrofluoride/petroleum ether. Dodecyl 6-deoxy-6-fluoro-alpha-D-glucopyranoside (13), prepared from the glucoside 12 with the fluorinating agent DAST, shows a narrow monotropic SA-phase and lyotropic liquid crystalline behaviour in contact with water. Dodecyl 6-deoxy-6-fluoro-beta-D-galactopyranoside (17), prepared in three steps from the acetal 14, does not form mesophases. The liquid crystalline behaviour of the amphiphilic glycosyl fluorides 3a-f, 7, and of the 6-deoxy-6-fluoro derivative 13 is described.

  DOI：

  10.1002/prac.19953370142
• 作为产物：
  描述：

  乙酸酐 、 6-O-Decyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 在 氢氟酸 作用下， 以 硝基甲烷 为溶剂， 反应 16.0h， 以96%的产率得到[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-2-(decoxymethyl)-6-fluorooxan-3-yl] acetate
  参考文献：
  名称：

  Reaktionen mit und in wasserfreiem Fluorwasserstoft 7.¹Von Isopropylidenzuckern zu acylierten Pyranosyl- oder Furanosylfluoriden in einem Schritt

  摘要：

  与无水氟化氢的反应 7.1 从异丙基糖到酰化吡喃糖和呋喃糖氟化物的一步法 一种便捷的单锅转化方法被描述，用于将6-O-取代的1,2:3,4-二-O-异丙基化α-D-半乳糖吡喃糖（1a-g）和3-O-取代的1,2:5,6-二-O-异丙基化α-D-葡萄糖呋喃糖（5a-c）转化为相应的6-O-取代的2,3,4-三-O-酰化α-D-半乳糖吡喃糖氟化物（2a-f, 3e, 3g）以及3-O-取代的2,5,6-三-O-乙酰化α/β-D-葡萄糖呋喃糖氟化物（6a-c）。这种简短的合成方法得益于新的均相试剂/催化剂/溶剂组合，包含无水氟化氢/硝基甲烷/羧酸酐（2:5:1-1.5）。未发现环收缩或扩展；此外，功能基团在2a-f, 3e, 3g的6位和6a-c的3位均表现出区域稳定性。

  DOI：

  10.1055/s-1991-26601