4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside | 38191-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside
• 英文别名: p-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside；p-nitrophenyl 2-acetamido-2-deoxy-α-D-pyranoside；pNP-α-ManNAc；N-[(2R,3S,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]acetamide
• CAS: 38191-71-8
• 化学式: C₁₄H₁₈N₂O₈
• 分子量: 342.306
• InChiKey: OMRLTNCLYHKQCK-ITGHMWBKSA-N

物化性质

• 沸点：
  694.7±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside 在 吡啶 作用下， 反应 120.0h， 生成 p-nitrophenyl-2-acetamido-3,4-benzoyl-6-O-trityl-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Utkina, N. S.; Eliseeva, A. V.; Nikolaev, A. V., Russian Journal of Bioorganic Chemistry, 1993, vol. 19, # 2, p. 127 - 133

  摘要：

  DOI：
• 作为产物：
  描述：

  N-acetyl-D-mannosamine 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 trifluoromethanesulfonic acid 、 硝酸 、 sodium methylate 作用下， 以 二氯甲烷 、 乙酸酐 、 溶剂黄146 为溶剂， 反应 72.33h， 生成 4-nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Facile synthesis of nitrophenyl 2-acetamido-2-deoxy-α-D-mannopyranosides from ManNAc-oxazoline

  摘要：

  描述了一种大规模制备o-和p-硝基苯基2-乙酰氨基-2-脱氧-α-D-甘露糖苷的合成方法。该合成途径采用苯酚与ManNAc oxazoline的糖基化，然后通过芳香基的硝化产生可分离的o-和p-硝基苯基衍生物混合物，比例为2:3。

  DOI：

  10.3762/bjoc.8.48

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。
• Synthesis of 4-Nitrophenyl 2-Acetamido-2-deoxy-β-D-mannopyranoside and 4-Nitrophenyl 2-Acetamido-2-deoxy-α-D-mannopyranoside
  作者：Pavel Krist、Marek Kuzma、István F. Pelyvás、Pavla Simerská、Vladimír Křen

  DOI：10.1135/cccc20030801

  日期：——

  The title compounds were synthesized by the selective reduction of the azido group in 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside (8) and 4-nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-mannopyranoside (11), and by subsequent acetylation. Compound8was prepared by opening of the epoxide ring in methyl 2,3-anhydro-4,6-O-benzylidene-α-D-glucopyranoside (1) with sodium azide, followed by inversion of the configuration at C-3 in the resulting altropyranoside and glycosidation with 4-nitrophenol.

  这些标题化合物是通过选择性还原4-硝基苯基3,4,6-三O-乙酰基-2-叠氮-2-脱氧-α-D-甘露聚糖 (8) 和 4-硝基苯基3,4,6-三O-乙酰基-2-叠氮-2-脱氧-β-D-甘露聚糖 (11) 中的叠氮基，并随后进行乙酰化合成的。 化合物8是通过用硝基苯酚对甲基2,3-环氧-4,6-O-苄基亚甲基-α-D-葡萄糖聚糖 (1) 进行环氧环开启，然后在产生的阿尔托吡喃糖中C-3处的构型倒置，最后与4-硝基苯酚进行糖苷化而制备的。
• Di and Tri saccharides, methods of making them and hair growth compositions containing them
  申请人：UNILEVER PLC

  公开号：EP0528624A1

  公开（公告）日：1993-02-24

  The preparation of a di or tri saccharide in which at least one glycoside residue bears an acetylamino substituent is catalysed enzymatically using an impure enzyme preparation with N-acetylhexosaminidase activity. The compounds produced, some of which are novel, may be useful to stimulate hair growth.

  使用具有N-乙酰己糖胺酸酶活性的不纯酶制备至少一个糖苷残基带有乙酰氨基取代基的二糖或三糖，产生的一些新化合物可能有助于刺激头发生长。
• 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。