1-[4-(hydroxymethyl)tetrahydro-2-thienyl]uracil

• 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: 1-[4-(hydroxymethyl)tetrahydro-2-thienyl]uracil
• 英文别名: 1-[(2S,4R)-4-(hydroxymethyl)tetrahydrothiophen-2-yl]pyrimidine-2,4-dione；1-[(2S,4R)-4-(hydroxymethyl)thiolan-2-yl]pyrimidine-2,4-dione
• 化学式: C₉H₁₂N₂O₃S
• 分子量: 228.272
• InChiKey: PWRZJDOKRZCFLN-SVRRBLITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (R)-tert-butyl((2,3-dihydrothiophen-3-yl)methoxy)diphenylsilane 在 三乙基硼 、 四丁基氟化铵 、 氧气 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 15.5h， 生成 1-[4-(hydroxymethyl)tetrahydro-2-thienyl]uracil
  参考文献：
  名称：

  Synthesis of 4′-thionucleosides by 1,3-dipolar cycloadditions of the simplest thiocarbonyl ylide with alkenes bearing electron-withdrawing groups

  摘要：

  Reactions of the simplest thiocarbonyl ylide with a variety of appropriate alkenes bearing electron-withdrawing substituents afforded the corresponding tetrahydrothiophenes, which could be easily elaborated into hydroxy and hydroxymethyl derivatives and then coupled with nucleobases to produce different 4 '-thionucleo sides. Particularly, alpha- and beta-anomers of 1-[3,4-bis(hydroxymethyl)tetrahydro-2-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with dimethyl fumarate and maleate, while 1-[4-(hydroxymethyl)tetrahydro-2-thienyl]- and 1-[4-(hydroxymethyl)tetrahydro-3-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with a chiral alpha,beta-unsaturated amide. These processes, simple in the experimental conditions and large availability of the starting materials, affording moderate to good yields of 4 '-thionucleosides, represent an optimum alternative to those, already known, based on sugars, which often have the drawbacks of a higher number of steps and lower yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.080

文献信息

• Synthesis of 4′-thionucleosides by 1,3-dipolar cycloadditions of the simplest thiocarbonyl ylide with alkenes bearing electron-withdrawing groups
  作者：Antonino Corsaro、Venerando Pistarà、Maria Assunta Chiacchio、Elisa Vittorino、Roberto Romeo

  DOI：10.1016/j.tetlet.2007.05.080

  日期：2007.7

  Reactions of the simplest thiocarbonyl ylide with a variety of appropriate alkenes bearing electron-withdrawing substituents afforded the corresponding tetrahydrothiophenes, which could be easily elaborated into hydroxy and hydroxymethyl derivatives and then coupled with nucleobases to produce different 4 '-thionucleo sides. Particularly, alpha- and beta-anomers of 1-[3,4-bis(hydroxymethyl)tetrahydro-2-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with dimethyl fumarate and maleate, while 1-[4-(hydroxymethyl)tetrahydro-2-thienyl]- and 1-[4-(hydroxymethyl)tetrahydro-3-thienyl]-thymine, -cytosine, -uracil and -fluorouracil were prepared with a chiral alpha,beta-unsaturated amide. These processes, simple in the experimental conditions and large availability of the starting materials, affording moderate to good yields of 4 '-thionucleosides, represent an optimum alternative to those, already known, based on sugars, which often have the drawbacks of a higher number of steps and lower yields. (c) 2007 Elsevier Ltd. All rights reserved.