1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3-diacetylglycerol | 213264-91-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3-diacetylglycerol
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,3-diacetyloxypropoxy)oxan-2-yl]methyl acetate
• CAS: 213264-91-6
• 化学式: C₂₁H₃₀O₁₄
• 分子量: 506.461
• InChiKey: FWIUOWWMLLPLFJ-OKNYXOPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3-diacetylglycerol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以96%的产率得到α-D-Glcp-(1->3)-D-glycerol
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465
• 作为产物：
  描述：

  allyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 1-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3-diacetylglycerol
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465

文献信息

• Montmorillonite K-10 as a Reusable Catalyst for Fischer Type of Glycosylation under Microwave Irradiation
  作者：Dipak K. Roy、Manobjyoti Bordoloi

  DOI：10.1080/07328300802107437

  日期：2008.7

  Montmorillonite K10 catalyzed Fischer type glycosylation was studied for various monosacharides with different alcohols under microwave irradiation. The method was found to be efficient, economic, simple and time saving and the catalyst montmorillonite K-10 was reused three times without loss of catalytic activity and anomeric selectivity. With glycerol, the method gave products glycosylated at primary

  在微波辐射下，研究了蒙脱石K10催化的费歇尔型糖基化反应，研究了用不同醇制得的各种单糖。发现该方法是有效，经济，简单和省时的，并且催化剂蒙脱石K-10可重复使用三次，而不会损失催化活性和端基异构体选择性。对于甘油，该方法仅产生在伯醇处糖基化的产物。