allyl 2,6-di-O-acetyl-3-O-benzyl-β-D-glucopyranoside | 150269-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,6-di-O-acetyl-3-O-benzyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-5-acetyloxy-3-hydroxy-4-phenylmethoxy-6-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 150269-83-3
• 化学式: C₂₀H₂₆O₈
• 分子量: 394.422
• InChiKey: IJUUFLKAIXUUCE-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 2,6-di-O-acetyl-3-O-benzyl-β-D-glucopyranoside 、 benzyl (2-O-acetyl-3-O-benzyl-4-O-p-methoxybenzyl-α-D-glucopyranosyl trichloroacetimidate)uronate 在 三氟甲磺酸三甲基硅酯 作用下， 以 甲苯 为溶剂， 反应 0.67h， 以96%的产率得到allyl 2,6-di-O-acetyl-3-O-benzyl-4-O-(benzyl 2-O-acetyl-3-O-benzyl-4-O-p-methoxybenzyl-β-D-glucopyranosiduronate)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a trisulfated heparan sulfate disaccharide analog and its use as a template for preliminary molecular imprinting studies

  摘要：

  A heparan sulfate disaccharide analog was synthesized by a multistep route. This synthesis was designed in such a way that one intermediate could be selectively deprotected to provide versatility during both synthesis and homologation of heparan sulfate related polysaccharides. Non-covalent imprinted polymers were prepared by using the synthesized disaccharide as a template and a primary amine functionalized acrylate as the key functional monomer suitable for specific sulfated sugar recognition. The binding of related sugars to the imprinted and non-imprinted polymers and the binding of template to the chemically modified polymers have been also investigated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.12.020
• 作为产物：
  描述：

  allyl 2-O-acetyl-3-O-benzyl-β-D-glucopyranoside 、 乙酰氯 以 吡啶 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 allyl 2,6-di-O-acetyl-3-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a trisulfated heparan sulfate disaccharide analog and its use as a template for preliminary molecular imprinting studies

  摘要：

  A heparan sulfate disaccharide analog was synthesized by a multistep route. This synthesis was designed in such a way that one intermediate could be selectively deprotected to provide versatility during both synthesis and homologation of heparan sulfate related polysaccharides. Non-covalent imprinted polymers were prepared by using the synthesized disaccharide as a template and a primary amine functionalized acrylate as the key functional monomer suitable for specific sulfated sugar recognition. The binding of related sugars to the imprinted and non-imprinted polymers and the binding of template to the chemically modified polymers have been also investigated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.12.020