3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran | 1373612-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran
• CAS: 1373612-90-8
• 化学式: C₁₄H₁₈O₆S
• 分子量: 314.359
• InChiKey: RHMHZYJRZVLWSY-ZOBORPQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran 在 氧气 、 sodium hydride 、 copper(l) chloride 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 8.5h， 生成 1-[3,5-di(benzyloxy)-(2S,3R,3aS,6aR)-perhydrofuro[3,2-b]furan-2-yl-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
• 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 、 碘 、 copper(II) sulfate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 16.0h， 生成 3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran
  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