N,N'-(2,5-二甲基-1,4-亚苯基)二[2-[(2,4-二氯苯基)偶氮]-3-羰基丁酰胺] | 72691-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: N,N'-(2,5-二甲基-1,4-亚苯基)二[2-[(2,4-二氯苯基)偶氮]-3-羰基丁酰胺]
• 英文名称: acetyl 2,3,4-tri-O-acetyl-6-O-triphenylmethyl-α-D-mannopyranoside
• 英文别名: 1,2,3,4-tetra-O-acetyl-6-O-triphenylmethyl-α-D-mannopyranose；1,2,3,4-tetra-O-acetyl-6-O-trityl-α-D-mannopyranose；O¹,O²,O³,O⁴-Tetraacetyl-O⁶-trityl-α-D-mannopyranose；1,2,3,4-Tetra-O-acetyl-6-O-trityl-a-D-mannopyranose；[(2R,3R,4S,5S,6R)-4,5,6-triacetyloxy-2-(trityloxymethyl)oxan-3-yl] acetate
• CAS: 72691-30-6
• 化学式: C₃₃H₃₄O₁₀
• 分子量: 590.627
• InChiKey: GTJGUFOLNHYRQE-KQLGDFJMSA-N

物化性质

• 沸点：
  633.3±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N,N'-(2,5-二甲基-1,4-亚苯基)二[2-[(2,4-二氯苯基)偶氮]-3-羰基丁酰胺] 在 三氟甲磺酸三甲基硅酯 、 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 10.02h， 生成 acetyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-2,3,4-tri-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Aldolase-Catalyzed Synthesis of β-d-Galp-(1→9)-d-KDN:  A Novel Acceptor for Sialyltransferases

  摘要：

  [graphics]beta-D-Galp-(1 -> 9)-D-KDN, a disaccharide component of the cell wall of Streptomyces sp. MB-8, was synthesized from beta-D-Galp-(1 -> 6)-D-Manp and pyruvate using a sialic acid aldolase. The obtained KDN-containing compound was a novel acceptor for bacterial sialyltransferases. Unusual alpha 2,3- and alpha 2,6-linked sialyltrisaccharides and a tetrasaccharide were synthesized using a one-pot two-enzyme system containing a Neisseria meningitidis CMP-sialic acid synthetase and a Pasteurella multocida sialyltransferase or a Photobacterium damsela alpha 2,6-sialyltransferase.

  DOI：

  10.1021/ol060736m
• 作为产物：
  描述：

  甘露糖 在 吡啶 作用下， 反应 1.5h， 生成 N,N'-(2,5-二甲基-1,4-亚苯基)二[2-[(2,4-二氯苯基)偶氮]-3-羰基丁酰胺]
  参考文献：
  名称：

  Aldolase-Catalyzed Synthesis of β-d-Galp-(1→9)-d-KDN:  A Novel Acceptor for Sialyltransferases

  摘要：

  [graphics]beta-D-Galp-(1 -> 9)-D-KDN, a disaccharide component of the cell wall of Streptomyces sp. MB-8, was synthesized from beta-D-Galp-(1 -> 6)-D-Manp and pyruvate using a sialic acid aldolase. The obtained KDN-containing compound was a novel acceptor for bacterial sialyltransferases. Unusual alpha 2,3- and alpha 2,6-linked sialyltrisaccharides and a tetrasaccharide were synthesized using a one-pot two-enzyme system containing a Neisseria meningitidis CMP-sialic acid synthetase and a Pasteurella multocida sialyltransferase or a Photobacterium damsela alpha 2,6-sialyltransferase.

  DOI：

  10.1021/ol060736m

文献信息

• Helferich; Leete, Chemische Berichte, 1929, vol. 62, p. 1549,1553, 1554
  作者：Helferich、Leete

  DOI：——

  日期：——
• The Synthesis of Certain Oligosaccharide Acetates in the Mannose Series¹
  作者：Delbert D. Reynolds、Wm. Lloyd Evans

  DOI：10.1021/ja01858a014

  日期：1940.1
• Design, Synthesis, and Biological Evaluation of Novel Carbohydrate-Based Sulfamates as Carbonic Anhydrase Inhibitors
  作者：Marie Lopez、Jonathan Trajkovic、Laurent F. Bornaghi、Alessio Innocenti、Daniela Vullo、Claudiu T. Supuran、Sally-Ann Poulsen

  DOI：10.1021/jm101525j

  日期：2011.3.10

  Carbonic anhydrases (CAs) IX and XII are enzymes with newly validated potential for the development of personalized, first-in-class cancer chemotherapies. Here we present the design and synthesis of novel carbohydrate-based CA inhibitors, several of which were very efficient inhibitors (K-i < 10 nM) with good selectivity for cancer-associated CA isozymes over off-target CA isozymes. All inhibitors comprised a carbohydrate core with one hydroxyl group derivatized as a sulfamate. Five different carbohydrates were chosen to present a selection of molecular shapes with subtle stereochernical differences to the CA enzymes active site. Variable modifications of the remaining sugar hydroxyl groups were incorporated to provide an incremental coverage of chemical property parameters that are associated with biopharmaceutical performance. All sulfamate inhibitors displayed ligand efficiencies that are consistent with those reported for good drug lead candidates.