6-O-Decyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside | 138188-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-O-Decyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
• 英文别名: (1S,2R,6R,8R,9S)-8-(decoxymethyl)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 138188-84-8
• 化学式: C₂₂H₄₀O₆
• 分子量: 400.556
• InChiKey: MQSPTFARSATTJJ-LCWAXJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-O-Decyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 1.5h， 以90%的产率得到
  参考文献：
  名称：

  半乳糖和氨基葡萄糖两亲肟的有效合成

  摘要：

  已合成并表征了半乳糖和葡糖胺的新型两亲肟。肟官能团已被引入非离子表面活性剂的第一和第六位置，该非离子表面活性剂由糖极性头和亲脂性侧链组成。该化合物可溶于吡啶，微溶于其他极性有机溶剂和水。

  DOI：

  10.1016/j.tetlet.2012.02.086
• 作为产物：
  描述：

  D-gulopyranose 在 咪唑 、 15-冠醚-5 、 硫酸 、 sodium hydride 、 copper(II) sulfate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 生成 6-O-Decyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Gosenca, Mirjam; Mravljak, Janez; Gasperlin, Mirjana, Acta Chimica Slovenica, 2013, vol. 60, # 2, p. 310 - 322

  摘要：

  DOI：

文献信息

• The efficient synthesis of amphiphilic oximes of galactose and glucosamine
  作者：Janez Mravljak、Aleš Obreza

  DOI：10.1016/j.tetlet.2012.02.086

  日期：2012.4

  New amphiphilic oximes of galactose and glucosamine have been synthesized and characterized. The oxime functionality has been introduced to the first and sixth positions of a nonionic surfactant, consisting of a sugar polar head and a lipophilic side chain. The compounds are soluble in pyridine and sparingly soluble in other polar organic solvents and water.

  已合成并表征了半乳糖和葡糖胺的新型两亲肟。肟官能团已被引入非离子表面活性剂的第一和第六位置，该非离子表面活性剂由糖极性头和亲脂性侧链组成。该化合物可溶于吡啶，微溶于其他极性有机溶剂和水。
• Reaktionen mit und in wasserfreiem Fluorwasserstoft 7.¹Von Isopropylidenzuckern zu acylierten Pyranosyl- oder Furanosylfluoriden in einem Schritt
  作者：Ralf Miethchen、Torsten Gabriel、Gundula Kolp

  DOI：10.1055/s-1991-26601

  日期：——

  Reactions with and in Anhydrous Hydrogen Fluoride 7.1 From Isopropylidene Sugars to Acylated Pyranosyl and Furanosyl Fluorides in One Step A convenient one-pot transformation of the 6-O-substituted 1,2:3,4-di-O-isopropylidene-α-D-galactopyranoses 1a-g and the 3-O-substituted 1,2:5,6-di-O-isopropylidene-α-D-glucofuranoses 5a-c is described to form the corresponding 6-O-substituted 2,3, 4-tri-O-acyl-α-D-galactopyranosyl fluorides 2a-f, 3e, 3g and 3-O-substituted 2,5,6-tri-O-acetyl-α/β-D-glucofuranosyl fluorides 6a-c, respectively. This short way of synthesis is possible by use of the new homogeneous reagent/catalyst/solvent combination composed of anhydrous hydrogen fluoride/nitromethane/carboxylic acid anhydride (2: 5:1-1.5). A ring contraction or extension is not found; in addition the functional groups are regiostable in 6-position of 2a-f, 3e, 3g and in 3-position of 6a-c, respectively.

  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。
• 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.
• Gosenca, Mirjam; Mravljak, Janez; Gasperlin, Mirjana, Acta Chimica Slovenica, 2013, vol. 60, # 2, p. 310 - 322
  作者：Gosenca, Mirjam、Mravljak, Janez、Gasperlin, Mirjana、Obreza, Ales

  DOI：——

  日期：——