N³,2′,3′-O-tris-(benzyloxycarbonyl)uridine | 1160622-73-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N³,2′,3′-O-tris-(benzyloxycarbonyl)uridine
• 英文别名: N(3)-2',3'-O-tris-(benzyloxycarbonyl)uridine；benzyl 3-[(2R,3R,4R,5R)-5-(hydroxymethyl)-3,4-bis(phenylmethoxycarbonyloxy)oxolan-2-yl]-2,6-dioxopyrimidine-1-carboxylate
• CAS: 1160622-73-0
• 化学式: C₃₃H₃₀N₂O₁₂
• 分子量: 646.607
• InChiKey: PAKVEIBFCNRYAX-YXINZVNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N³,2′,3′-O-tris-(benzyloxycarbonyl)uridine 在 Pd(OH)2/C 、 1,3-环己二烯 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 尿嘧啶核苷
  参考文献：
  名称：

  Simultaneous Removal of Benzyl and Benzyloxycarbonyl Protective Groups in 5′-O-(2-Deoxy-α-D-Glucopyranosyl)Uridine by Catalytic Transfer Hydrogenolysis

  摘要：

  Synthesis of N3,2',3'-O-tris-(benzyloxycarbonyl)uridine and its use in the synthesis of 5'-O-(2-deoxy--d-glucopyranosyl)uridine is described. Simultaneous removal of benzyl and benzyloxycarbonyl groups was accomplished by catalytic transfer hydrogenolysis in the presence of Pearlman's catalyst without competing side reactions.

  DOI：

  10.1080/15257770802458303
• 作为产物：
  描述：

  在 tetrafluoroboric acid 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以1.41 g的产率得到N³,2′,3′-O-tris-(benzyloxycarbonyl)uridine
  参考文献：
  名称：

  Simultaneous Removal of Benzyl and Benzyloxycarbonyl Protective Groups in 5′-O-(2-Deoxy-α-D-Glucopyranosyl)Uridine by Catalytic Transfer Hydrogenolysis

  摘要：

  Synthesis of N3,2',3'-O-tris-(benzyloxycarbonyl)uridine and its use in the synthesis of 5'-O-(2-deoxy--d-glucopyranosyl)uridine is described. Simultaneous removal of benzyl and benzyloxycarbonyl groups was accomplished by catalytic transfer hydrogenolysis in the presence of Pearlman's catalyst without competing side reactions.

  DOI：

  10.1080/15257770802458303

文献信息

• Synthesis and Preliminary Biological Evaluations of 5′-Substituted Derivatives of Uridine as Glycosyltransferase Inhibitors
  作者：Jadwiga Paszkowska、Katarzyna Kral、Tadeusz Bieg、Urszula Nawrot、Wiesław Szeja、Ilona Wandzik

  DOI：10.3390/molecules18078018

  日期：——

  New derivatives of uridine which contain a b-ketoenol motif were synthesized, characterized and biologically tested. Synthesized compounds 1–4 showed no activity against bovine milk β-1,4-galactosyltransferase I at concentrations up to 2.0 mM and were not active against Candida albicans and Aspergilus fumigatus up to the maximum tested concentration of 1,000 µg/mL.

  合成、表征和生物学测试了含有 β-酮烯醇基序的新型尿苷衍生物。合成化合物 1-4 在浓度高达 2.0 mM 时对牛乳 β-1,4-半乳糖基转移酶 I 没有活性，在最高测试浓度 1,000 µg/mL 时对白色念珠菌和烟曲霉没有活性。
• Synthesis of 2-deoxy-hexopyranosyl derivatives of uridine as donor substrate analogues for glycosyltransferases
  作者：Ilona Wandzik、Tadeusz Bieg、Marianna Czaplicka

  DOI：10.1016/j.bioorg.2009.08.001

  日期：2009.12

  A series of 2-deoxy-hexopyranosyl derivatives of uridine have been synthesized as analogues of UDP-sugar. These compounds were tested as inhibitors against bovine β-1,4-galactosyltransferase I in fluorescent assays and showed no significant inhibition.

  已经合成了一系列尿苷的2-脱氧-己吡喃糖基衍生物，作为UDP-糖的类似物。这些化合物在荧光测定法中作为牛β-1,4-半乳糖基转移酶I的抑制剂进行了测试，未显示出明显的抑制作用。
• Simultaneous Removal of Benzyl and Benzyloxycarbonyl Protective Groups in 5′-<i>O</i>-(2-Deoxy-<b>α</b>-D-Glucopyranosyl)Uridine by Catalytic Transfer Hydrogenolysis
  作者：Ilona Wandzik、Tadeusz Bieg、Monika Kadela

  DOI：10.1080/15257770802458303

  日期：2008.11.13

  Synthesis of N3,2',3'-O-tris-(benzyloxycarbonyl)uridine and its use in the synthesis of 5'-O-(2-deoxy--d-glucopyranosyl)uridine is described. Simultaneous removal of benzyl and benzyloxycarbonyl groups was accomplished by catalytic transfer hydrogenolysis in the presence of Pearlman's catalyst without competing side reactions.