3-O-acetyl-6-O-benzyl-1,2-O-[(S)-1-(methoxycarbonyl)ethylidene]-α-D-glucopyranoside | 1065698-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3-O-acetyl-6-O-benzyl-1,2-O-[(S)-1-(methoxycarbonyl)ethylidene]-α-D-glucopyranoside
• 英文别名: methyl (2S,3aR,5R,6R,7S,7aR)-7-acetyloxy-6-hydroxy-2-methyl-5-(phenylmethoxymethyl)-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-2-carboxylate
• CAS: 1065698-14-7
• 化学式: C₁₉H₂₄O₉
• 分子量: 396.394
• InChiKey: QOMRTZVALUBILP-ZXDRVLLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-6-O-benzyl-1,2-O-[(S)-1-(methoxycarbonyl)ethylidene]-α-D-glucopyranoside 在 三氟甲磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl-(1→4)-6-O-acetyl-2,3-di-O-benzoyl-β-D-galactopyranosyl-(1→4)-3-O-acetyl-6-O-benzyl-1,2-O-[(S)-1-(methoxycarbonyl)ethylidene]-α-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of a multivalent heterobifunctional ligand for specific interaction with Shiga toxin 2 produced by E. coli O157:H7

  摘要：

  Hemolytic uremic syndrome is a potentially fatal complication of food poisoning caused by Escherichia coli O157:H7, especially those strains that produce the Stx2 Shiga toxin. Multivalent inhibitors based on the P-k trisaccharide are most effective against Stx1 the less dangerous of the two Shiga toxins. Inhibitors containing a terminal 2-acetamido-2-deoxy-alpha-D-galactopyranosyl residue in place of the terminal alpha-D-galactopyranosyl residue of P-k trisaccharide have been shown to exhibit preferential binding to Stx2. A multivalent heterobifunctional P-k analog containing 2-acetamido-2-deoxy-alpha-D-galactopyranose has been synthesized in a format that facilitates the ablation of toxin activity via supramolecular complex formation between Stx and the endogenous protein, Human serum amyloid P component (HuSAP). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.05.010
• 作为产物：
  描述：

  3,4,6-Tri-O-acetyl-1,2-O-<(1-exo-cyano)ethylidene>-α-D-glucopyranose 在 吡啶 、 三乙基硅烷 、 camphor-10-sulfonic acid 、 sodium 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 51.5h， 生成 3-O-acetyl-6-O-benzyl-1,2-O-[(S)-1-(methoxycarbonyl)ethylidene]-α-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of a multivalent heterobifunctional ligand for specific interaction with Shiga toxin 2 produced by E. coli O157:H7

  摘要：

  Hemolytic uremic syndrome is a potentially fatal complication of food poisoning caused by Escherichia coli O157:H7, especially those strains that produce the Stx2 Shiga toxin. Multivalent inhibitors based on the P-k trisaccharide are most effective against Stx1 the less dangerous of the two Shiga toxins. Inhibitors containing a terminal 2-acetamido-2-deoxy-alpha-D-galactopyranosyl residue in place of the terminal alpha-D-galactopyranosyl residue of P-k trisaccharide have been shown to exhibit preferential binding to Stx2. A multivalent heterobifunctional P-k analog containing 2-acetamido-2-deoxy-alpha-D-galactopyranose has been synthesized in a format that facilitates the ablation of toxin activity via supramolecular complex formation between Stx and the endogenous protein, Human serum amyloid P component (HuSAP). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.05.010

文献信息

• Multivalent Heterobifunctional Polymers And Methods Of Their Use
  申请人：Bundle David R.

  公开号：US20100166695A1

  公开（公告）日：2010-07-01

  Designed herein are multivalent heterobifunctional polymers for binding to a biological target exhibiting biological activity and to an effector template which can affect the biological activity of the biological target or detect the presence of the biological target. The polymers comprise a plurality of pre-arranged heterobifunctional ligands connected thereto, and each heterobifunctional ligand comprises a first functionality capable of binding to the biological target, and a second functionality capable of binding to the effector template. The heterobifunctional ligands are pre-arranged on the polymer so as to form a ternary complex between the polymer, the biological target and the effector template. The polymers, methods and compositions described herein provide an approach for the design and production of new therapeutic agents as well as agents useful in a variety of non-therapeutic applications.

  本文设计了一种多价异源双功能聚合物，用于与表现出生物活性的生物靶标和能够影响生物靶标生物活性或检测生物靶标存在的效应模板结合。聚合物包括多个预先排列的异源双功能配体，每个异源双功能配体包括能够结合生物靶标的第一功能和能够结合效应模板的第二功能。异源双功能配体在聚合物上预先排列，以形成聚合物、生物靶标和效应模板之间的三元复合物。本文所描述的聚合物、方法和组合物提供了一种设计和生产新治疗剂以及在各种非治疗应用中有用的剂的方法。
• WO2008/116293
  申请人：——

  公开号：——

  公开（公告）日：——