2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-acetoxybenzyl(3-methoxy-4-acetoxy)benzoate | 18265-35-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-acetoxybenzyl(3-methoxy-4-acetoxy)benzoate
• 英文别名: 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-acetyloxybenzyl benzoate；salireposide pentaacetate；(4-acetoxy-2-benzoyloximethyl-phenyl)-(tetra-O-acetyl-β-D-glucopyranoside)；(4-Acetoxy-2-benzoyloxymethyl-phenyl)-(tetra-O-acetyl-β-D-glucopyranosid)；Salireposide, pentaacetate；[5-acetyloxy-2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyphenyl]methyl benzoate
• CAS: 18265-35-5
• 化学式: C₃₀H₃₂O₁₄
• 分子量: 616.576
• InChiKey: ORVFWCUSTYLGLY-OVFYEYCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-acetoxybenzyl(3-methoxy-4-acetoxy)benzoate 在 盐酸 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 4.0h， 以40%的产率得到2'-O-acetyl-salireposide
  参考文献：
  名称：

  The first example of a one-step synthesis of 2′-O-acetyl aryl-d-glucopyranosides

  摘要：

  A selective acidic system for partial deacetylation of phenolic D-glucopyranosides per-acetates has been developed that allows synthesis of the corresponding 2'-O-acetyl-D-glucosides. Many disadvantages of generally used methods for preparing such mono-acyl derivatives involving multistep procedures or the use of enzymes are avoided. The ion at m/z 289 in mass spectra of their TMS derivatives indicates a particular and characteristic fragmentation pattern of these 2'-O-acetyl derivatives of D-glucopyranosides. Quantum-chemical calculations applying B3LYP/TZVP level of theory revealed the stability of 2'-O-acetyl glucopyranoside if compare with 3'-, 4'- and 6'- O-acetyl glucopyanosides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.03.017
• 作为产物：
  描述：

  4-乙酰氧基苯酚 在 吡啶 、 sodium tetrahydroborate 、 十六烷基三甲基溴化铵 、 三氟乙酸 、 silver(l) oxide 作用下， 以 喹啉 、 氯仿 、 水 为溶剂， 反应 28.0h， 生成 2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-5-acetoxybenzyl(3-methoxy-4-acetoxy)benzoate
  参考文献：
  名称：

  水杨科一些酚糖苷的天然酰基衍生物的第一全化学合成。

  摘要：

  水杨科的某些天然酚类糖苷的总合成，即：salireposide，populosides A，B和C，而在植物中不存在脱氧水杨苷（2-（β-D-吡喃葡萄糖基氧基）-苄基苯甲酸酯）和异水杨苷的过乙酸（2-（β-D-吡喃葡萄糖基氧基）-5-苯甲酰氧基苄醇），是从容易获得的酚和葡萄糖开始的。开发了一种简单的合成2-酰氧基水杨基和龙胆醇的酚苷衍生物的方法。这些天然产物合成的关键步骤是在其他酰基存在下选择性除去乙酰基。

  DOI：

  10.1016/j.carres.2012.10.006

文献信息

• Communications. Studies on the Barks of the Family Salicaceae. II. Salireposide from the Bark of Populus tremuloides
  作者：Irwin Pearl、Stephen Darling

  DOI：10.1021/jo01092a045

  日期：1959.10
• First total chemical synthesis of natural acyl derivatives of some phenolglycosides of the family Salicaceae
  作者：Maxim L. Belyanin、Elena V. Stepanova、Vladimir D. Ogorodnikov

  DOI：10.1016/j.carres.2012.10.006

  日期：2012.12

  readily available phenols and glucose was accomplished. A simple method for the synthesis of phenolglycosides derivatives of 2-acyloxy salicyl and gentisyl alcohol was developed. The key step of these natural products' synthesis is a selective removal of acetyl groups in the presence of other acyl groups.

  水杨科的某些天然酚类糖苷的总合成，即：salireposide，populosides A，B和C，而在植物中不存在脱氧水杨苷（2-（β-D-吡喃葡萄糖基氧基）-苄基苯甲酸酯）和异水杨苷的过乙酸（2-（β-D-吡喃葡萄糖基氧基）-5-苯甲酰氧基苄醇），是从容易获得的酚和葡萄糖开始的。开发了一种简单的合成2-酰氧基水杨基和龙胆醇的酚苷衍生物的方法。这些天然产物合成的关键步骤是在其他酰基存在下选择性除去乙酰基。
• The first example of a one-step synthesis of 2′-O-acetyl aryl-d-glucopyranosides
  作者：Elena V. Stepanova、Maxim L. Belyanin、Victor D. Filimonov、Rashid R. Valiev、Margit Gruner、Victor Rogachev

  DOI：10.1016/j.carres.2015.03.017

  日期：2015.5

  A selective acidic system for partial deacetylation of phenolic D-glucopyranosides per-acetates has been developed that allows synthesis of the corresponding 2'-O-acetyl-D-glucosides. Many disadvantages of generally used methods for preparing such mono-acyl derivatives involving multistep procedures or the use of enzymes are avoided. The ion at m/z 289 in mass spectra of their TMS derivatives indicates a particular and characteristic fragmentation pattern of these 2'-O-acetyl derivatives of D-glucopyranosides. Quantum-chemical calculations applying B3LYP/TZVP level of theory revealed the stability of 2'-O-acetyl glucopyranoside if compare with 3'-, 4'- and 6'- O-acetyl glucopyanosides. (C) 2015 Elsevier Ltd. All rights reserved.