1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-cyano-6-phenyl-2-thiouracil | 289906-51-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-cyano-6-phenyl-2-thiouracil
• 英文别名: 5-cyano-6-phenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-thiouracil；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(5-cyano-4-oxo-6-phenyl-2-sulfanylidenepyrimidin-1-yl)oxan-2-yl]methyl acetate
• CAS: 289906-51-0
• 化学式: C₂₅H₂₅N₃O₁₀S
• 分子量: 559.554
• InChiKey: HZDJYURSGVTJPY-BKSKZGTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  203
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-cyano-6-phenyl-2-thiouracil 反应 1.0h， 以18%的产率得到2,2'-anhydro-2-mercapto-6-phenyl-1-(3,4,6-tri-O-acetyl-β-D-mannopyranosyl)pyrimidin-5(2H)-one
  参考文献：
  名称：

  A direct synthetic approach to uracil anhydrothionucleoside derivatives

  摘要：

  Direct conversion of peracylated N-1-(beta-D-glucopyranosyl)-2-thiouracil derivatives into the corresponding anhydrothionucleosides has been studied under various conditions including: gas-phase pyrolysis, heating without a solvent, and by heating in a solvent of high boiling point (DPE) in the presence of a base (DABCO) and reaction in a microwave reactor. Heating at 210-220 degrees C was found to give the best yield of a single isomer. The structures of the new anhydrothionucleosides were confirmed by NMR techniques. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.09.006
• 作为产物：
  描述：

  1,2,3,4-四氢-4-氧代-6-苯基-2-硫代-5-嘧啶甲腈 在 硫酸氢铵 、 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-5-cyano-6-phenyl-2-thiouracil
  参考文献：
  名称：

  A Facile Synthesis of 6-Aryl-5-cyano-1-(β-d-pyranosyl or β-d-furanosyl)-2-thiocytosines

  摘要：

  The treatment of a piperidinium salt of 6-aryl-5-cyano-2-thiouracil with an O-peracetyl-alpha -D-pyranosyl bromide produces a mixture of N1-(beta -D-pyranosyl)-2-thiouracil and its N1,S-2-disubstituted analog. By contrast, the reaction of a silyl derivative of the 2-thiouracil with an O-pcracetyl-beta -D-pyranose furnishes the mononucleoside selectively. Both the mononucleoside/dinucleoside mixture and pure mononucleoside undergo ammonolysis under mild conditions to give the P-D-nucleoside of 6-aryl-5-cyano-2-thiocytosine. The silyl method also provides an easy access to beta -D-ribosyl nucleosides. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00807-3

文献信息

• The first direct ammonolysis of 2-thiouracil nucleosides to 2-thiocytosine nucleosides
  作者：Lucjan Strekowski、Ibrahim M Abdou、Adel M.E Attia、Steven E Patterson

  DOI：10.1016/s0040-4039(00)00712-7

  日期：2000.6

  Sugar-peracetylated 1-(beta-D-glucopyranosyl)-, 1-(beta-D-galactopyranosyl)-, and 1-(beta-D-xylopyranosyl)-6-aryl-5-cyano-2-thiouracils 2-4 and the corresponding 1-pyranosyl-2-(pyranosylthio)pyrimidines 5-7 undergo efficient ammonolysis (NH3/MeOH, 0-->23 degrees C, 16 h) to give the corresponding 1-(beta-D-pyranosyl)-6-aryl-5-cyano-2-thiocytosines. (C) 2000 Elsevier Science Ltd. All rights reserved.