Octyl-β-D-glucofuranoside | 158604-09-2

• 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: Octyl-β-D-glucofuranoside
• 英文别名: Octyl beta-D-glucofuranoside；(2R,3R,4R,5R)-2-[(1R)-1,2-dihydroxyethyl]-5-octoxyoxolane-3,4-diol
• CAS: 158604-09-2
• 化学式: C₁₄H₂₈O₆
• 分子量: 292.373
• InChiKey: VZLNXIZRQPJOEU-DHGKCCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-glucurono-6,3-lactone 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 17.5h， 生成 Octyl-β-D-glucofuranoside
  参考文献：
  名称：

  一些长链烷基-D-呋喃葡萄糖苷-6,3-内酯，D-呋喃呋喃糖苷及其衍生物的合成及性能

  摘要：

  通过酸催化葡糖醛酸-6,3-内酯的糖基化反应合成了几个长链烷基-D-D-呋喃呋喃葡萄糖基-6,3-内酯。使烷基β-D-葡糖呋喃二葡萄糖基-6,3-内酯与硼氢化钠反应，得到相应的烷基β-D-葡糖呋喃糖苷；与2-氨基乙醇和N，N-二甲基乙二胺反应，得到相应的烷基-N-（2 -羟乙基）-β-D-葡糖基呋喃二磺酰胺和烷基-N- [2-（二甲基氨基）乙基]-β-D-葡糖基呋喃二磺酰胺。用碘甲烷将十二烷基-N- [2-（二甲基氨基）乙基]-β-D-呋喃呋喃二氨基甲酰胺季铵化，得到碘化铵。这些新化合物和一些代表性衍生物的特征是1 H-和13 C-NMR光谱。还测定了其中一些化合物的物理性质（液晶行为，表面张力，CMC）。

  DOI：

  10.1002/recl.19941130203

文献信息

• A new synthesis of O-glycosides from totally O-unprotected glycosyl donors
  作者：Vincent Ferrières、Jean-Noël Bertho、Daniel Plusquellec

  DOI：10.1016/0040-4039(95)00356-h

  日期：1995.4

  O-unprotected aldoses (D-glucose, D-galactose and D-mannose) and D-fructose in THF or 1,4-dioxane using anhydrous FeCl3 as promoter afforded either aldofuranosides 1, 3, 4 in good overall yields or exclusively β-D-fructopyranosides 7. Conversely α-D-aldopyranosides 2, 5 and 6 were obtained respectively from D-glucose, D-mannose and N-acetyl-D-glucosamine when the reactions were performed in the presence

  Ó的完全的-Glycosidation ø -unprotected醛糖（d葡萄糖，d半乳糖和d甘露糖），使用无水的FeCl在THF或1,4-二恶烷和d-果糖3作为助催化剂，得到任一aldofuranosides 1，3，4在良好的整体产量或仅β-D-果糖吡喃糖苷7。相反地，当在BF 3 .OEt 2的存在下在超声条件下进行反应时，分别从D-葡萄糖，D-甘露糖和N-乙酰基-D-葡萄糖胺获得α-D-醛糖吡喃二糖苷2、5和6。
• Composition in the form of an oil-in water emulsion containing a silicone copolymer and showing a liquid crystalline phase and uses thereof
  申请人：L'OREAL

  公开号：US20030105169A1

  公开（公告）日：2003-06-05

  A composition in the form of an oil-in-water emulsion containing, in a physiologically acceptable medium, an oily phase dispersed in an aqueous phase, the aqueous phase containing particles of a noncrosslinked silicone copolymer and at least one amphiphilic surfactant capable of forming liquid crystals.

  一种水包油型乳液组合物，在生理上可接受的介质中，油相分散在水相中，水相含有非交联硅氧烷共聚物颗粒和至少一种能形成液晶的两性表面活性剂。
• 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
• Glycosylation mediated—BAIL in aqueous solution
  作者：Sébastien Delacroix、Jean-Pierre Bonnet、Matthieu Courty、Denis Postel、Albert Nguyen Van Nhien

  DOI：10.1016/j.carres.2013.08.009

  日期：2013.11

  The use of Bronsted acid ionic liquid (BAIL) as a catalyst for the activation of unreactive and unprotected glycosyl donors has been demonstrated for the first time in aqueous solution. (c) 2013 Elsevier Ltd. All rights reserved.
• Estrogenicity of Octyl Glucoside Synthesized by Direct Glucosidation as Non-Endocrine Disruptive Surfactant
  作者：Kyong-Hwan Chung、Hangun Kim、Young-Kwon Park、Byung-Hoon Kim、Jung-Sik Kim、Sang-Chul Jung

  DOI：10.1166/jnn.2018.14875

  日期：2018.2.1

  The estrogenicity of octyl glucoside was studied with its preparation method using microporous zeolites. Its estrogenicity was estimated using E-assay method to confirm the possibility as non-endocrine disruptive surfactant. The octyl glucoside was synthesized from D-glucose with 1-octanol by direct glucosidation. The high conversion of D-glucose was obtained on H-FAU zeolite which has a mild acid strength. The conversion and yield were improved with increasing of acid site amount of the zeolite catalysts. The octyl glucopyranoside is more hydrophilic than nonylphenol and has a high wettability. The octyl glucosides represented extremely lower estrogenic cell proliferation compared with nonylphenol.