5,6-Anhydro-1,2-O-isopropylidene-3-O-octyl-α-D-glucofuranose | 160835-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-Anhydro-1,2-O-isopropylidene-3-O-octyl-α-D-glucofuranose
• 英文别名: (3aR,5R,6S,6aR)-2,2-dimethyl-6-octoxy-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 160835-31-4
• 化学式: C₁₇H₃₀O₅
• 分子量: 314.422
• InChiKey: PIDCMKIHGVJPSS-IBEHDNSVSA-N

物化性质

• 沸点：
  382.2±42.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-Anhydro-1,2-O-isopropylidene-3-O-octyl-α-D-glucofuranose 在 四丁基溴化铵 、 potassium carbonate 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.5h， 生成 1-[[(2R,3R,4S,5R)-3,5,6-trihydroxy-4-octoxyoxan-2-yl]methyl]-3,4-dihydro-1,4-benzodiazepine-2,5-dione
  参考文献：
  名称：

  Synthesis and amphiphilic properties of glycosyl-1,4-benzodiazepin-2,5-diones

  摘要：

  Glycosyl-l,4-benzodiazepin-2,5-diones were prepared by coupling polyhydroxylated groups at N-1 of the corresponding benzodiazepine. The groups include 1-deoxy-D,L-xylit-1-yl, 6-deoxy-D-glucopyranos-6-yl, and 6-deoxy-3-O-R-D-glucopyranos-6-yl (R = n-CnH2n+1 n = 8, 12, and 16). The structural variations of the sugar group allowed comparison of such amphiphilic data as water solubility (Sw), critical micelle concentration (CMC), and corresponding surface tension (gamma) values. At 25 degrees C, unsubstituted benzodiazepines have Sw values from 0.9 to 4.2 10(-3) mol L-1, whereas xylit-1-yl and 6-deoxy-D-glucopyranos-6-yl derivatives are, respectively, 7.4-25 and 58-204 times more soluble. Also, compounds with R = n-C8H17 are more soluble than corresponding benzodiazepines (1.4-5.8 times) and give micelles with CMC from 2.7 to 5.6 10-3 mol L-1 and corresponding gamma from 29 to 37 mN m(-1). In contrast, compounds with R = n-C12H25 and n-C16H33 are not soluble enough to reach the critical micelle concentration. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00163-4
• 作为产物：
  描述：

  3-O-n-Octyl-1,2-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 反应 49.0h， 生成 5,6-Anhydro-1,2-O-isopropylidene-3-O-octyl-α-D-glucofuranose
  参考文献：
  名称：

  Goueth, Pierre Y.; Ronco, Gino; Villa, Pierre, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 679 - 696

  摘要：

  DOI：

文献信息

• Synthesis and Amphiphilic Behavior of<i>N</i>,<i>N</i>‐Bis‐glucosyl‐1,5‐benzodiazepin‐2,4‐dione
  作者：Brahim Lakhrissi、El Mokhtar Essassi、Mohamed Massoui、Gérard Goethals、Vincent Lequart、Eric Monflier、Roméo Cecchelli、Patrick Martin

  DOI：10.1081/car-200039373

  日期：2004.12.27

  Glucosyl‐1,5‐benzodiazepin‐2,4‐diones were synthesized in order to study the influence of the glucidic moiety on the amphiphilic behaviour. The glucosyl groups include 6‐deoxy‐D‐glucopyranos‐6‐yl and 6‐deoxy‐3‐O‐R‐D‐glucopyranos‐6‐yl (R = n − C n H 2n+1; n = 1, 8, 10 and 12). Variation in the length of the hydrocarbon chain allowed comparison of such amphiphilic data as water solubility (Sw) and surface

  为了研究糖基部分对两亲性行为的影响，合成了糖基-1,5-苯并二氮杂-2,4-二酮。葡糖基团包括6-脱氧d -glucopyranos -6-基和6-脱氧-3- ö -R- d -glucopyranos -6-基（R =  ñ  -  c ^ ñ ħ 2 Ñ 1 ; Ñ  = 1， 8、10和12）。烃链长度的变化允许比较两亲数据，例如水溶性（Sw）和表面张力（γ）值。在25°C时，R = H和CH 3的吡喃葡萄糖基苯并二氮杂 与起始的1,5-苯并二氮杂-2,4-二酮相比，水溶性更高。在D-吡喃葡萄糖的C-3碳原子上具有适当烷基链的其他一些葡萄糖基苯并二氮杂苯衍生物在相应的饱和度下具有可变的水溶性和接近43至46 mN·m -1的表面张力γ值。此外，根据初步测试，这些化合物似乎对血脑屏障显示出更好的亲和力。
• Towards the synthesis of new benzimidazolone derivatives with surfactant properties
  作者：Brahim Lakhrissi、Abdelhafid Benksim、Mohamed Massoui、El Mokhtar Essassi、Vincent Lequart、Nicolas Joly、Daniel Beaupère、Anne Wadouachi、Patrick Martin

  DOI：10.1016/j.carres.2007.11.028

  日期：2008.2

  New water-soluble benzimidazolone derivatives were synthesized. In the first approach, di-N-glycosyl and mono-N-alkyl-N-glycosyl compounds were obtained by grafting C-6-activated glycosides onto benzimidazolone. In the second approach, benzimidazolone derivatives bearing a glucosyl unit were synthesized using an efficient glycosylation method. Every compound structure was confirmed by means of NMR spectroscopy and elemental analysis. The preliminary surfactant properties of some compounds were evaluated. (c) 2007 Elsevier Ltd. All rights reserved.
• Glycosyl-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones. Synthesis, Tensioactivity and Anitbacterial Activity
  作者：Patrick Martin、Driss Bouhlal、Paul Godé、Gérard Goethals、Mohamed Massoui、Pierre Villa

  DOI：10.3987/com-00-9093

  日期：——