6-(1,2-dihydroxyethyl)-2,2-dimethyl-4-(4-methylphenylsulfonyloxymethyl)-(3aR,4R,6aS)-perhydrofuro[3,4-d][1,3]dioxole | 1373612-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(1,2-dihydroxyethyl)-2,2-dimethyl-4-(4-methylphenylsulfonyloxymethyl)-(3aR,4R,6aS)-perhydrofuro[3,4-d][1,3]dioxole
• 英文别名: [(3aS,4R,6R,6aR)-4-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl 4-methylbenzenesulfonate
• CAS: 1373612-85-1
• 化学式: C₁₇H₂₄O₈S
• 分子量: 388.439
• InChiKey: NAQNIOIOWDHGSS-QCODTGAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-(1,2-dihydroxyethyl)-2,2-dimethyl-4-(4-methylphenylsulfonyloxymethyl)-(3aR,4R,6aS)-perhydrofuro[3,4-d][1,3]dioxole 在 咪唑 、 硫酸 、 水 、 碘 、 氧气 、 sodium hydride 、 三苯基膦 、 copper(l) chloride 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 10.5h， 生成 1-[3,5-di(benzyloxy)-(2R,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 、 4-二甲氨基吡啶 、 bismuth(III) chloride 、 硫酸 、 potassium tert-butylate 、 copper(II) sulfate 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 14.0h， 生成 6-(1,2-dihydroxyethyl)-2,2-dimethyl-4-(4-methylphenylsulfonyloxymethyl)-(3aR,4R,6aS)-perhydrofuro[3,4-d][1,3]dioxole
  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