n-octyl α-D-glucofuranoside | 166021-55-2

• 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: n-octyl α-D-glucofuranoside
• 英文别名: Octyl alpha-D-glucofuranoside；(2R,3R,4R,5S)-2-[(1R)-1,2-dihydroxyethyl]-5-octoxyoxolane-3,4-diol
• CAS: 166021-55-2
• 化学式: C₁₄H₂₈O₆
• 分子量: 292.373
• InChiKey: VZLNXIZRQPJOEU-KSTCHIGDSA-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：

  辛醇 、 葡萄糖 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以15%的产率得到n-octyl α-D-glucofuranoside
  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 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。
• 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.
• 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