methyl 2,3,4-tri-O-benzyl-6-O-dodecyl-α-D-glucopyranoside | 142025-33-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-dodecyl-α-D-glucopyranoside
• CAS: 142025-33-0
• 化学式: C₄₀H₅₆O₆
• 分子量: 632.881
• InChiKey: FPHPLYFGTBEUAO-DTQLOPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.05
• 重原子数：
  46.0
• 可旋转键数：
  23.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-dodecyl-α-D-glucopyranoside 在 palladium on activated charcoal 甲醇 、 三氟甲磺酸酐 、 氢气 、 sodium methylate 、 乙酸酐 作用下， 以 甲醇 为溶剂， 生成 6-O-lauryl-D-glucose
  参考文献：
  名称：

  Amphiphilic and mesogenic carbohydrates - II. sysnthesis and Characterisation of mono-o-(n-alkyl)-d-glucose derivates

  摘要：

  The synthesis of various amphiphilic o-(n-alkyl)-D-glucopyranoses, having the long alkyl chain (C8H17 - C16H33) in 2-, 3-, 4- or 6-position are described. The investigations of the thermal behaviour of 6-o-(13a-e), 4-o-(14a-e), 3-o-(15a-e) and 2-o-(n-alkyl)-D-glucopyranoses (16a-e) and the corresponding methyl-alpha-D-glucosides 4a-e, 8a-e and 12a-e, respectively, are summarized in this paper.

  DOI：

  10.1016/s0040-4020(01)92248-3
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 甲酸 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 、 paraffin oil 为溶剂， 反应 26.25h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-dodecyl-α-D-glucopyranoside
  参考文献：
  名称：

  甲基葡苯二糖苷的羟烷基醚的疏水性和亲水性平衡及其对中间相行为的影响

  摘要：

  制备了四个系列的单取代甲基α- D-吡喃葡萄糖苷羟烷基醚，并根据其疏水-亲水平衡对其分子结构进行了研究，研究了它们的热致和溶致自组织特性。获得的结果使我们对驱动凝聚软物质相形成的力有了新的认识。

  DOI：

  10.1002/chem.201202933

文献信息

• Organofluorine compounds and fluorinating agents. 14. Thermotropic Liquid-Crystalline Glycosyl Fluorides
  作者：Ralf Miethchen、Cornelia Zur

  DOI：10.1002/prac.19953370142

  日期：——

  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.