2,3,4-tri-O-benzyl-rhamnopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzyl-rhamnopyranose
• 英文别名: 6-Methyl-3,4,5-tris(phenylmethoxy)oxan-2-ol
• 化学式: C₂₇H₃₀O₅
• 分子量: 434.532
• InChiKey: YRAQXZMHYZXWBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-rhamnopyranose 、 苯丙炔酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以33.333%的产率得到
  参考文献：
  名称：

  金（III）催化的使用苯丙丙酸酯糖苷的糖基化：苯丙酸，一个易于分离和可重复使用的离开基团

  摘要：

  使用新合成的台式稳定苯丙酸苯丙酯糖基（PPG）供体，开发了一种有效且操作简单的金（III）催化的糖基化方案。金（III）催化的PPG活化与各种基于碳水化合物和非碳水化合物的糖基受体进行得很好，并导致其相应的O / N-糖苷的收率好至极好，并具有可重复使用和易于分离的苯丙酸的再生。差异保护的PPG在优化的反应条件下反应良好。特别地，在甘露糖基和鼠李糖基PPG供体上观察到良好的异头选择性。初步的机理研究表明，与酯基相邻的三键的存在对于激活至关重要，并且基于PPG的供体显示出比类似的乙酸和苯甲酸酯供体更高的反应性。

  DOI：

  10.1021/acs.joc.8b02422

文献信息

• Linkable Lewis X Analogs
  申请人：Ranganathan Ramachandran

  公开号：US20080300220A1

  公开（公告）日：2008-12-04

  Disclosed herein is a class of linkable tetrasaccharide compounds that includes the amino phenyl glycoside of sialyl Lewis X (SLe X ) and related analogs. These compounds have conjugatable nucleophilic groups, making them useful in preparing multimeric SLe X compositions. In particular, the disclosed SLe X compounds can be used to prepare selectin binding ligand conjugates by linking them to a reporter moiety, such as a contrast agent, a radiodiagnostic agent, or a cytotoxic or chemotherapeutic agent. The SLe X compounds and conjugates of the invention exhibit binding to selectin that is similar to native Sialyl Le X , and are, therefore, useful for diagnosing and treating selectin-mediated disorders and related conditions.

  本发明涉及一类可连接的四糖化合物，其中包括唾液酸Lewis X（SLeX）的氨基苯基糖苷和相关类似物。这些化合物具有可共轭的亲核基团，使它们在制备多聚SLeX组分方面非常有用。特别是，所披露的SLeX化合物可用于通过将它们连接到报告者基团（如对比剂、放射诊断剂或细胞毒素或化学治疗剂）来制备选择素结合配体共轭物。本发明的SLeX化合物和共轭物表现出与天然唾液酸LeX类似的选择素结合性，因此，它们对于诊断和治疗选择素介导的疾病和相关病症非常有用。
• LINKABLE LEWIS X ANALOGS
  申请人：Ranganathan Ramachandran

  公开号：US20110229409A1

  公开（公告）日：2011-09-22

  Disclosed herein is a class of linkable tetrasaccharide compounds that includes the amino phenyl glycoside of sialyl Lewis X (SLe X ) and related analogs. These compounds have conjugatable nucleophilic groups, making them useful in preparing multimeric SLe X compositions. In particular, the disclosed SLe X compounds can be used to prepare selectin binding ligand con-jugatcs by linking them to a reporter moiety, such as a contrast agent, a radiodiagnostic agent, or a cytotoxic or chemotherapeutic agent. The SLe X compounds and conjugates of the invention exhibit binding to selectin that is similar to native Sialyl Le X , and are, therefore, useful for diagnosing and treating selectin-mediated disorders and related conditions.

  本文披露了一类可连接四糖化合物，其中包括唾液酸Lewis X（SLeX）的氨基苯基糖苷和相关类似物。这些化合物具有可共轭的亲核基团，因此它们在制备多聚SLeX组分方面是有用的。特别地，所披露的SLeX化合物可用于通过将它们与报告物质（如对比剂、放射性诊断剂或细胞毒素或化疗剂）连接起来，制备选择素结合配体共轭物。本发明的SLeX化合物和共轭物表现出与天然唾液酸LeX相似的选择素结合性，因此可用于诊断和治疗选择素介导的疾病和相关病症。
• PHENYL C-GLUCOSIDE DERIVATIVE CONTAINING DEOXYGLUCOSE STRUCTURE, PREPARATION METHOD AND USES THEREOF
  申请人：Tianjin Institute Of Pharmaceutical Research

  公开号：EP3246324A2

  公开（公告）日：2017-11-22

  The present invention provides a phenyl C-glucoside derivative containing a deoxyglucose structure as represented by formula I, preparation method thereof, a pharmaceutical composition comprising the same, and uses thereof in the preparation of medicaments for treating diabetes, wherein substituents R1-R7 are as defined in the specification. The present invention also provides a method for synthesizing the phenyl C-glucoside derivative containing a deoxyglucose structure and an intermediate product. The method has advantages of being simple to manage and of low cost, which is suitable for large-scale industrial production. The present invention further provides a cocrystal of (1S)-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-1,6-dideoxy-D-glucose and L-proline, and preparation method and uses thereof.

  本发明提供了一种由式I表示的含有脱氧葡萄糖结构的苯基C-葡萄糖苷衍生物、其制备方法、包含其的药物组合物以及其在制备治疗糖尿病药物中的用途，其中取代基R1-R7如说明书中所定义。本发明还提供了一种合成含有脱氧葡萄糖结构的苯基 C-葡萄糖苷衍生物和中间产物的方法。该方法具有操作简单、成本低的优点，适合大规模工业化生产。本发明进一步提供了一种(1S)-1-[4-氯-3-(4-乙氧基苄基)苯基]-1,6-二脱氧-D-葡萄糖和 L-脯氨酸的共晶体及其制备方法和用途。
• Phenyl c-glucoside derivative containing deoxyglucose structure, preparation method and use thereof
  申请人：Tianjin Institute of Pharmaceutical Research

  公开号：US10294259B2

  公开（公告）日：2019-05-21

  The present invention provides a phenyl C-glucoside derivative containing a deoxyglucose structure as represented by formula I, preparation method thereof, a pharmaceutical composition comprising the same, and uses thereof in the preparation of medicaments for treating diabetes, wherein substituents R1-R7 are as defined in the specification. The present invention also provides a method for synthesizing the phenyl C-glucoside derivative containing a deoxyglucose structure and an intermediate product. The method has advantages of being simple to manage and of low cost, which is suitable for large-scale industrial production. The present invention further provides a cocrystal of (1S)-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-1,6-dideoxy-D-glucose and L-proline, and preparation method and uses thereof.

  本发明提供了一种由式I表示的含有脱氧葡萄糖结构的苯基C-葡萄糖苷衍生物、其制备方法、包含其的药物组合物以及其在制备治疗糖尿病药物中的用途，其中取代基R1-R7如说明书中所定义。本发明还提供了一种合成含有脱氧葡萄糖结构的苯基 C-葡萄糖苷衍生物和中间产物的方法。该方法具有操作简单、成本低的优点，适合大规模工业化生产。本发明进一步提供了一种(1S)-1-[4-氯-3-(4-乙氧基苄基)苯基]-1,6-二脱氧-D-葡萄糖和 L-脯氨酸的共晶体及其制备方法和用途。
• PHENYL C-GLUCOSIDE DERIVATIVE CONTAINING DEOXYGLUCOSE STRUCTURE, PREPARATION METHOD AND USE THEREOF
  申请人：Tianjin Institute of Pharmaceutical Research

  公开号：US20170057989A1

  公开（公告）日：2017-03-02

  The present invention provides a phenyl C-glucoside derivative containing a deoxyglucose structure as represented by formula I, preparation method thereof, a pharmaceutical composition comprising the same, and uses thereof in the preparation of medicaments for treating diabetes, wherein substituents R 1 -R 7 are as defined in the specification. The present invention also provides a method for synthesizing the phenyl C-glucoside derivative containing a deoxyglucose structure and an intermediate product. The method has advantages of being simple to manage and of low cost, which is suitable for large-scale industrial production. The present invention further provides a cocrystal of (1S)-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-1,6-dideoxy-D-glucose and L-proline, and preparation method and uses thereof.