(methyl 5',6'-dideoxy-2',3'-isopropylidene-6'-β-D-ribo-5'-ene-hexofuranuronate)-1-uracil | 73108-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (methyl 5',6'-dideoxy-2',3'-isopropylidene-6'-β-D-ribo-5'-ene-hexofuranuronate)-1-uracil
• 英文别名: methyl (E)-3-[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]prop-2-enoate
• CAS: 73108-55-1
• 化学式: C₁₅H₁₈N₂O₇
• 分子量: 338.317
• InChiKey: LAMQAUAHQXRHFC-OTFKQHBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (methyl 5',6'-dideoxy-2',3'-isopropylidene-6'-β-D-ribo-5'-ene-hexofuranuronate)-1-uracil 在 sodium hydroxide 、 barium hydroxide octahydrate 、 次氯酸叔丁酯 、 4 A molecular sieve 、 三氟化硼乙醚 、 四丁基碘化铵 、 碳酸氢钠 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 丙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 37.0h， 生成
  参考文献：
  名称：

  卡巴唑的全合成，卡巴霉素抗结核抗生素的核心结构。

  摘要：

  DOI：

  10.1002/anie.200462439
• 作为产物：
  描述：

  2',3'-O-isopropylidene-uridine-5'-carboxylic acid 在 N-甲基吗啉 、 间氯过氧苯甲酸 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (methyl 5',6'-dideoxy-2',3'-isopropylidene-6'-β-D-ribo-5'-ene-hexofuranuronate)-1-uracil
  参考文献：
  名称：

  Stereocontrolled radical reactions in carbohydrate and nucleoside chemistry.

  摘要：

  The radicals, generated by photolysis of 2,3-dimethyl ketals of N-hydroxy-2- thiopyridone uronic esters, reacted stereoselectively with electron deficient olefins leading to highly functionalised chain-elongated pentafuranosides, hexapyranosides and pentafuranosyl-nucleosides through the 4,5 and 4' radicals, respectively.

  DOI：

  10.1016/s0957-4166(00)86288-6

文献信息

• Synthesis of isoxazolidine-containing uridine derivatives as caprazamycin analogues
  作者：Mayumi Yamaguchi、Akira Matsuda、Satoshi Ichikawa

  DOI：10.1039/c4ob02142h

  日期：——

  antibacterial nucleoside natural products, was conducted by scaffold-hopping of the structurally complex diazepanone moiety to the isoxazolidine scaffold. The designed isoxazolidine-containing uridine derivatives were synthesized by an intramolecular 1,3-dipolar cycloaddition of alkenyl nitrone as a key step. The lactone-fused isoxazolidine intermediate was easily converted to the target compounds by

  通过将结构复杂的二氮杂one酮部分跃迁到异恶唑烷骨架上，简化了有前途的抗菌核苷天然产物辣椒素的简化。通过烯内酮的分子内1，3-偶极环加成反应合成了设计的含异恶唑烷的尿苷衍生物。内酯稠合的异恶唑烷中间体通过亲核取代和亲电子封端所得伯醇使内酯部分开环后，通过依次引入关键取代基，可以轻松地将其转化为目标化合物。几种类似物对流感嗜血杆菌ATCC 10211（MIC 0.25-0.5杯mL（-1））表现出良好的活性，对耐万古霉素的屎肠球菌SR7914（MIC 4-8杯mL（-1））表现出中等的活性。
• Synthesis of Caprazamycin Analogues and Their Structure−Activity Relationship for Antibacterial Activity
  作者：Shinpei Hirano、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1021/jo702264e

  日期：2008.1.1

  Synthesis of palmitoyl caprazol 7, which possesses a simple fatty acyl side chain at the 3"'-position of the diazepanone moiety, was carried out and their antibacterial activity was evaluated. The key elements of our approach include the improved synthesis of the key 5'-p-0-aminoribosyl-glycyluridine derivative, installation of the palmitoyl side chain to the cyclization precursor, and the construction of the diazepanone by an intramolecular reductive amination. The second generation synthesis of (+)-caprazol was also established. Palmitoyl caprazol 7 exhibited antibacterial activity against Mycobacterium smegmatis ATCC607 (MIC = 6.25 mu g/mL) with potency similar to that of the caprazamycins (CPZs). Palmitoyl caprazol 7 and N-6'-desmethyl palmitoyl caprazol 28 also exhibited antibacterial activity against drug-resistant bacteria including methyciline-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (VRE) strains (MIC = 3.13-12.5 mu g/mL).
• Total Synthesis of Caprazol, a Core Structure of the Caprazamycin Antituberculosis Antibiotics
  作者：Shinpei Hirano、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1002/anie.200462439

  日期：2005.3.11
• Stereocontrolled radical reactions in carbohydrate and nucleoside chemistry.
  作者：Derek H.R. Barton、Stephane D. Géro、Béatrice Quiclet-Sire、Mohammad Samadi

  DOI：10.1016/s0957-4166(00)86288-6

  日期：1994.11

  The radicals, generated by photolysis of 2,3-dimethyl ketals of N-hydroxy-2- thiopyridone uronic esters, reacted stereoselectively with electron deficient olefins leading to highly functionalised chain-elongated pentafuranosides, hexapyranosides and pentafuranosyl-nucleosides through the 4,5 and 4' radicals, respectively.