allyl 3-O-benzyl-4,6-di-O-p-methoxybenzylidene-β-D-glucopyranoside | 765910-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 3-O-benzyl-4,6-di-O-p-methoxybenzylidene-β-D-glucopyranoside
• 英文别名: (2R,4aR,6R,7R,8R,8aR)-2-(4-methoxyphenyl)-8-phenylmethoxy-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 765910-21-2
• 化学式: C₂₄H₂₈O₇
• 分子量: 428.482
• InChiKey: PUWSKJUBEVABQR-TZNXUKFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 3-O-benzyl-4,6-di-O-p-methoxybenzylidene-β-D-glucopyranoside 在 chromium(VI) oxide 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 乙酸肼 、 sodium cyanoborohydride 、 碳酸氢钠 、 高碘酸 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.0h， 生成 methyl (allyl 3-O-benzyl-2-O-pivaloyl-β-D-glucopyranosyl)uronate
  参考文献：
  名称：

  迈向糖胺聚糖的模块化合成：使用高碘酸氧化法合成透明质酸二糖结构单元

  摘要：

  描述了用于透明质酸固相组装的两个差异保护的GluNAc-β（1→4）-GluA和GluA-β（1→3）-GluNAc二糖模块的合成。高碘酸/三氧化铬氧化是促进葡萄糖从葡萄糖中获取葡萄糖醛酸部分的关键转化方法，应在伯醇的氧化中得到广泛应用。

  DOI：

  10.1016/j.tet.2004.06.037
• 作为产物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 、 allyl 3-O-benzyl-β-D-glucopyranoside 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以75%的产率得到allyl 3-O-benzyl-4,6-di-O-p-methoxybenzylidene-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

文献信息

• Toward the modular synthesis of glycosaminoglycans: synthesis of hyaluronic acid disaccharide building blocks using a periodic acid oxidation
  作者：Emma R. Palmacci、Peter H. Seeberger

  DOI：10.1016/j.tet.2004.06.037

  日期：2004.8

  The synthesis of two differentially protected GluNAc-β(1→4)-GluA and GluA-β(1→3)-GluNAc disaccharide modules for the solid-phase assembly of hyaluronic acid are described. A periodic acid/chromium trioxide oxidation was the key transformation to facilitate access to the glucuronic acid moiety from glucose and should find wide application in the oxidation of primary alcohols.

  描述了用于透明质酸固相组装的两个差异保护的GluNAc-β（1→4）-GluA和GluA-β（1→3）-GluNAc二糖模块的合成。高碘酸/三氧化铬氧化是促进葡萄糖从葡萄糖中获取葡萄糖醛酸部分的关键转化方法，应在伯醇的氧化中得到广泛应用。
• Synthesis of a trisulfated heparan sulfate disaccharide analog and its use as a template for preliminary molecular imprinting studies
  作者：Yasunori Ikeda、Fernando Siñeriz、Laurent Bultel、Eric Grand、José Kovensky、Dulce Papy-Garcia

  DOI：10.1016/j.carres.2007.12.020

  日期：2008.3

  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.