n-dodecyl β-D-galactofuranosiduronic acid

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: n-dodecyl β-D-galactofuranosiduronic acid
• 英文别名: (2S)-2-[(2R,3R,4R,5R)-5-dodecoxy-3,4-dihydroxyoxolan-2-yl]-2-hydroxyacetic acid
• 化学式: C₁₈H₃₄O₇
• 分子量: 362.464
• InChiKey: DLUSHRDJFBEIMG-XLKGFZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  半乳糖醛酸 、 十二烷醇 在 三氯化铁 、 calcium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以65%的产率得到n-dodecyl β-D-galactofuranosiduronic acid
  参考文献：
  名称：

  A convenient synthesis of alkyl d-glycofuranosiduronic acids and alkyl d-glycofuranosides from unprotected carbohydrates

  摘要：

  O-Glycosylation of a variety of long chain alcohols with totally unprotected uronic acids (D-glucuronic and D-galacturonic acids) and neutral carbohydrates (D-glucose, D-galactose, D-mannose and D-glucofuranurono-6,3-lactone), performed in heterogeneous media and promoted by Lewis acids (ferric chloride or boron trifluoride diethyl etherate), afforded alkyl D-glycofuranosiduronic acids and alkyl D-glycofuranosides, respectively, in high yields. Both chemoselectivity and anomeric stereoselectivity were enhanced by complexing agents, i.e. calcium or barium chloride. (C) 1998 Elsevier Science Ltd. All rights reserved

  DOI：

  10.1016/s0008-6215(98)00197-9

文献信息

• A new synthesis of<scp>D</scp>-glycosiduronates from unprotected<scp>D</scp>-uronic acids
  作者：Jean-Nöel Bertho、Vincent Ferrières、Daniel Plusquellec

  DOI：10.1039/c39950001391

  日期：——

  O-Glycosidation of totally O-unprotected D-galacturonic acid 1 in THF provides α-pyranosides 4a when promoted with BF3·OEt2 whereas β-furanosides 6β were obtained in the presence of FeCl3; when the same reaction is performed with D-glucuronic acid 2 or ‘D-glucurone’3, alkyl-D-glucofuranosidurono-6,3-lactones 7 are synthesized in excellent yields and high β-selectivity.

  在THF中对完全未保护的D-半乳糖醛酸1进行O-糖苷化，在BF3·OEt2的促进下得到α-吡喃苷4a，而在FeCl3存在下得到β-呋喃苷6β；当对D-葡糖醛酸2或“D-葡糖醛”3进行相同反应时，合成了优良收率和高β选择性的烷基-D-葡萄呋喃糖醇酸内酯7。
• Synthesis, physico-chemical properties and complexing abilities of new amphiphilic ligands from d-galacturonic acid
  作者：Anas Allam、Jean-Bernard Behr、Laurent Dupont、Véronique Nardello-Rataj、Richard Plantier-Royon

  DOI：10.1016/j.carres.2010.01.009

  日期：2010.4

  achieved. The anomeric ratio of the products was studied based on the main experimental parameters and the activation mode (thermal or microwave). In the second step, aminolysis of the n-octyl ester was achieved with various functionalized primary amines under standard thermal or microwave activation. The physico-chemical properties of these new amphiphilic ligands were measured and these compounds were found

  本文描述了由d-半乳糖醛酸和正辛醇（可再生原料）分两步轻松，高效地合成新型络合表面活性剂的方法。第一步，在费歇尔条件下实现了同时的O-糖基化-酯化。根据主要的实验参数和活化方式（热或微波）研究了产物的异头比。第二步，在标准的热或微波活化下，用各种官能化的伯胺实现正辛酯的氨解。测量了这些新的两亲性配体的物理化学性质，发现这些化合物表现出令人感兴趣的表面性质。通过EPR滴定研究了一种被吡啶部分官能化的脲酰胺配体对Cu（II）离子的络合能力。还合成并表征了固体化合物，从光谱数据推导了其相对结构。
• Thermotropic liquid-crystalline properties of some novel hexuronic acid derivatives bearing a single or two alkyl chains
  作者：Xavier Auvray、Bernard Labulle、Claude Petipas、Jean-Noël Bertho、Thierry Benvegnu、Daniel Plusquellec

  DOI：10.1039/a607305k

  日期：——

  We have recently developed a new method forO-glycosidation of totally O-unprotected aldoses and uronic acids. Either pyranosides or the corresponding furanosidic isomers are thus obtained in one step from natural carbohydrates. This paper is concerned with the thermotropic liquid-crystalline phases of alkyl β-d-galacto-(or gluco)-furanosiduronic acids bearing a saturated alkyl chain at the anomeric position and of some dialkylated derivatives. Phase identifications and measurements of phase transition data were carried out by differential scanning calorimetry (DSC), polarizing optical microscopy and small angle X-ray diffraction studies. Uronic derivatives have quite crystalline structures; upon heating, these compounds exhibit a smectic A* transformation.

  我们最近开发了一种新方法，用于对完全无 O 保护的醛酸和尿酸进行 O-糖苷化反应。这样就可以一步从天然碳水化合物中获得吡喃糖苷或相应的呋喃糖苷异构体。本文研究的是烷基 β-d-半乳糖（或葡萄糖）-呋喃糖苷酸的热致液晶相，这些烷基β-d-半乳糖（或葡萄糖）-呋喃糖苷酸的同分异构体和一些二烷基化衍生物的热致液晶相。通过差示扫描量热法（DSC）、偏振光学显微镜和小角 X 射线衍射研究，对这些衍生物进行了相鉴别和相变数据测量。 Uronic 衍生物具有相当结晶的结构；在加热时，这些化合物会出现 A* 的胶状转变。
• A convenient synthesis of alkyl d-glycofuranosiduronic acids and alkyl d-glycofuranosides from unprotected carbohydrates
  作者：Vincent Ferrières、Jean-Noël Bertho、Daniel Plusquellec

  DOI：10.1016/s0008-6215(98)00197-9

  日期：1998.9

  O-Glycosylation of a variety of long chain alcohols with totally unprotected uronic acids (D-glucuronic and D-galacturonic acids) and neutral carbohydrates (D-glucose, D-galactose, D-mannose and D-glucofuranurono-6,3-lactone), performed in heterogeneous media and promoted by Lewis acids (ferric chloride or boron trifluoride diethyl etherate), afforded alkyl D-glycofuranosiduronic acids and alkyl D-glycofuranosides, respectively, in high yields. Both chemoselectivity and anomeric stereoselectivity were enhanced by complexing agents, i.e. calcium or barium chloride. (C) 1998 Elsevier Science Ltd. All rights reserved