2,3,4-Tri-O-benzyl-6-desoxy-α-D-galactopyranosylbromid | 154968-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-Tri-O-benzyl-6-desoxy-α-D-galactopyranosylbromid
• 英文别名: (2R,3R,4S,5S,6R)-2-bromo-6-methyl-3,4,5-tris(phenylmethoxy)oxane
• CAS: 154968-66-8
• 化学式: C₂₇H₂₉BrO₄
• 分子量: 497.429
• InChiKey: MJZXQAVNDOYDAP-GJVZRYLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 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：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3,4-Tri-O-benzyl-6-desoxy-α-D-galactopyranosylbromid 、 1,6-Anhydro-2,4-di-O-benzyl-β-D-galactopyranose 生成 (1R,2S,3S,4R,5R)-3-[(2S,3R,4S,5S,6R)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-2,4-bis(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octane
  参考文献：
  名称：

  SPIJKER, NYNKE M.;VAN, BOECKEL CONSTANT A. A., ANGEW. CHEM. , 103,(1991) N, C. 179-182

  摘要：

  DOI：

文献信息

• Linkable sialyl lewis x analogs
  申请人：——

  公开号：US20040097403A1

  公开（公告）日：2004-05-20

  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.

  本文披露了一类可连接的四糖化合物，包括唾液酸Lewis X（SLeX）的氨基苯基糖苷及相关类似物。这些化合物具有可共轭的亲核基团，使它们在制备多聚SLeX组分时非常有用。具体而言，披露的SLeX化合物可用于通过将它们与报告基团（如对比剂、放射诊断剂或细胞毒性或化疗剂）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相似的选择素结合能力，因此对于诊断和治疗选择素介导的疾病及相关病症非常有用。
• Unexpected phenomena in glycosylations of acceptors with <i>L</i> -idose configuration
  作者：Nynke M. Spijker、Jan E. M. Basten、Constant A. A. van Boeckel

  DOI：10.1002/recl.19931121202

  日期：——

  coupling of the corresponding D-glucopyranosyl donor 19 with 13 led to a much higher β/α ratio (2/1). By changing the conformation of the acceptor into the 1,6-anhydro-L-idopyranose acceptor 23, 90% of the desired β-coupled disaccharide was obtained in the glycosylation with galactopyranosyl donor 12. Finally it was found that the α/β ratio of the condensation with 25, promoted by an insoluble silver salt

  为了合成Galß（1 4）IdoA二糖1，在不同条件下，用不同保护的D-吡喃半乳糖基供体进行L-艾杜糖酸衍生物5和13和L-吡喃葡萄糖衍生物21的几个糖基化反应。已经发现，即使当供体在C-2处包含一个参与基团时，这些偶联反应也主要导致不希望的α-糖苷间键的形成。另一方面，相应的D-吡喃葡萄糖基供体19与13的偶联导致更高的β/α比（2/1）。通过将受体的构型改变为1,6-脱水-L-吡喃葡萄糖受体23，用半乳糖吡喃糖基供体12进行糖基化反应后，可获得90％的所需β偶联二糖。最终发现，由不溶性银盐促进的与25的缩合的α/β比以不寻常的方式受到半乳糖基溴化物上取代基的影响。
• 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。
• Spijker, Nynke M.; Boeckel, Constant A. A. van, Angewandte Chemie, 1991, vol. 103, # 2, p. 179 - 182
  作者：Spijker, Nynke M.、Boeckel, Constant A. A. van

  DOI：——

  日期：——