1,3-di-O-benzyl-2-O-β-D-glucopyranosyl-sn-glycerol | 250608-15-2

• 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: 1,3-di-O-benzyl-2-O-β-D-glucopyranosyl-sn-glycerol
• 英文别名: (2R,3R,4S,5S,6R)-2-[1,3-bis(phenylmethoxy)propan-2-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 250608-15-2
• 化学式: C₂₃H₃₀O₈
• 分子量: 434.486
• InChiKey: YMYRXOZFKYAJTQ-XNBWIAOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3-di-O-benzyl-2-O-β-D-glucopyranosyl-sn-glycerol 在 palladium on activated charcoal 吡啶 、 Pseudomonas cepacia lipase 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 15.25h， 生成 1-O-decanoyl-2-O-β-D-glucopyranosyl-sn-glycerol
  参考文献：
  名称：

  Chemoenzymatic synthesis and antitumor promoting activity of 6′- and 3-esters of 2- O -β- d -glucosylglycerol

  摘要：

  Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.

  DOI：

  10.1016/s0968-0896(99)00137-6
• 作为产物：
  描述：

  1,3-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到1,3-di-O-benzyl-2-O-β-D-glucopyranosyl-sn-glycerol
  参考文献：
  名称：

  Chemoenzymatic synthesis and antitumor promoting activity of 6′- and 3-esters of 2- O -β- d -glucosylglycerol

  摘要：

  Through a simple chemoenzymatic approach 6'- and 3-esters of 2-O-beta-D-glucosylglycerol 1, with short-medium length fatty acid acyl chains, were prepared. The study of their in vitro antitumor promoting effect on Epstein-Barr virus early antigen (EBV-EA) activation, in comparison with that of the 1-esters previously described, confirms the significant activity of such monoacylated glycoglycerolipid analogues and establishes for the glucose series that the 1-substitution and the hexanoyl chain are the proper structural features for the maximum activity.

  DOI：

  10.1016/s0968-0896(99)00137-6

文献信息

• Short Regioselective Chemoenzymatic Synthesis and Biological Evaluation of 1-<i>O</i>-Acyl-2-<i>O</i>-(β-<scp>D</scp>-sulfoquinovopyranosyl)-<i>sn</i>-glycerols
  作者：Milind Dangate、Laura Franchini、Fiamma Ronchetti、Takanari Arai、Akira Iida、Harukuni Tokuda、Diego Colombo

  DOI：10.1002/ejoc.200900943

  日期：2009.12

  convenient chemoenzymatic synthesis of a new class of non-natural sulfo-glycolipids – 2-O-(β-D-sulfoquinovosyl)-monoacylglycerols (2-O-β-D-SQMG) – derived from 2-O-(β-D-glucopyranosyl)glycerol and carrying acyl chains ofvarious lengths at the 1-position of the sn-glycerol moiety, was performed with the aid of a key step involving regioselective lipase-catalyzed acylation of 2-O-(6-deoxy-6-tosyl-β-D-gl

  一种新型非天然磺基糖脂的便捷化学酶促合成 – 2-O-(β-D-磺基奎诺糖基)-单酰基甘油 (2-O-β-D-SQMG) – 衍生自 2-O-(β- D-吡喃葡萄糖基）甘油和在 sn-甘油部分的 1-位携带不同长度的酰基链，是在涉及区域选择性脂肪酶催化的 2-O-（6-脱氧-6-）酰化的关键步骤的帮助下进行的。甲苯磺酰基-β-D-吡喃葡萄糖基)-sn-甘油 (4) 在其 1 位，首次在此报道。在未保护的伯羟基和仲羟基存在下，通过选择性插入的甲苯磺酰基的硫代乙酸酯取代和随后的 Oxone®氧化来制备糖部分，有效地提供了目标化合物，己酰基、十二酰基和十八酰基衍生物 1a–c，在 EBV-EA 体外抗肿瘤启动子试验中测试时，它们是有活性的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Synthesis of <i>N</i>-oxyamide analogues of protein kinase B (Akt) targeting anionic glycoglycerolipids and their antiproliferative activity on human ovarian carcinoma cells
  作者：Marco Zuccolo、Giulia Orsini、Martina Quaglia、Luca Mirra、Cristina Corno、Nives Carenini、Paola Perego、Diego Colombo

  DOI：10.1039/d3ob00891f

  日期：——

  N-Oxyamides of bioactive anionic glycoglycerolipids based on 2-O-β-D-glucosylglycerol were efficiently prepared. However, the oxidation step of the primary hydroxyl group of the glucose moiety in the presence of the N-oxyamide function appeared to be a difficult task that was nevertheless conveniently achieved for the first time by employing a chemoenzymatic laccase/TEMPO procedure. The obtained N-oxyamides

  有效制备了基于2- O -β- D-葡萄糖基甘油的生物活性阴离子甘油脂的N-草酰胺。然而，在N-草酰胺官能团存在下，葡萄糖部分的伯羟基的氧化步骤似乎是一项艰巨的任务，但首次通过采用化学酶漆酶/TEMPO程序方便地实现了这一任务。与相应的生物活性酯类似，所获得的N-羟基酰胺在无血清培养基中比在完全培养基中表现出更高的对卵巢癌IGROV-1细胞增殖的抑制作用。稳定性和血清结合研究表明，在完全培养基中观察到的化合物活性降低可能主要是由于血清蛋白的结合作用，而不是糖甘油脂酰基链的水解降解。此外，无血清条件下的细胞研究结果表明，N-羟基酰胺基团可以增加甘油糖脂的抗增殖活性，而与阴离子羧基的存在无关。除 IGROV-1 之外的其他细胞系的细胞研究也支持该系列化合物对 Akt 过度激活的肿瘤细胞具有一定程度的选择性。