1-[3,5-dihydroxy-(2S,3R,3aR,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-5-methyl-1,2,3,4-tetrahydro-2,4-pyrimidinedione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1-[3,5-dihydroxy-(2S,3R,3aR,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-5-methyl-1,2,3,4-tetrahydro-2,4-pyrimidinedione
• 英文别名: 1-[[(3aR,5S,6R,6aR)-2,6-dihydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-5-yl]methyl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₂H₁₆N₂O₆
• 分子量: 284.269
• InChiKey: OSWMPIIOFPMYIM-SEMOWUPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-甘露糖 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 bismuth(III) chloride 、 硫酸 、 potassium tert-butylate 、 水 、 氢气 、 碘 、 氧气 、 palladium(II) hydroxide 、 sodium hydride 、 copper(II) sulfate 、 三苯基膦 、 copper(l) chloride 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 27.5h， 生成 1-[3,5-dihydroxy-(2S,3R,3aR,6aR)-perhydrofuro[3,2-b]furan-2-yl-methyl]-5-methyl-1,2,3,4-tetrahydro-2,4-pyrimidinedione
  参考文献：
  名称：

  Synthesis of N-homobicyclic dideoxynucleoside analogues

  摘要：

  Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by fractional crystallization. The two stereoisomers were converted to bicyclic furanolactols each of which was coupled with three nucleoside bases. Further debenzylations gave the six target N-homobicyclic dideoxynucleosides. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.018

文献信息

• Synthesis of N-homobicyclic dideoxynucleoside analogues
  作者：N. Raghavendra Swamy、N. Suryakiran、P. Paradesi Naidu、Y. Venkateswarlu

  DOI：10.1016/j.carres.2012.01.018

  日期：2012.5

  Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by fractional crystallization. The two stereoisomers were converted to bicyclic furanolactols each of which was coupled with three nucleoside bases. Further debenzylations gave the six target N-homobicyclic dideoxynucleosides. (C) 2012 Elsevier Ltd. All rights reserved.