[((2R,4R,5R)-4,5-Dihydroxy-2-methylsulfanyl-tetrahydro-thiopyran-2-yl)-difluoro-methyl]-phosphonic acid diethyl ester

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: [((2R,4R,5R)-4,5-Dihydroxy-2-methylsulfanyl-tetrahydro-thiopyran-2-yl)-difluoro-methyl]-phosphonic acid diethyl ester
• 英文别名: diethyl 2-(4,5-dihydroxy-2-methylsulfanyl-3,4,5,6-tetrahydro-4H-thiopyranyl)-difluoromethylphosphonate；(3R,4R,6R)-6-[diethoxyphosphoryl(difluoro)methyl]-6-methylsulfanylthiane-3,4-diol
• 化学式: C₁₁H₂₁F₂O₅PS₂
• 分子量: 366.387
• InChiKey: BOEVQLYQAYQQAW-KXUCPTDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  二氟甲基膦酸二乙酯 在 osmium (III) chloride 奎宁环 、 potassium carbonate 、 potassium hexacyanoferrate(III) 、 lithium diisopropyl amide 作用下， 以 水 、 叔丁醇 为溶剂， 反应 15.0h， 生成 [((2R,4R,5R)-4,5-Dihydroxy-2-methylsulfanyl-tetrahydro-thiopyran-2-yl)-difluoro-methyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of thiapyranoside precursors using the building-block approach from a phosphonodifluorodithioacetate

  摘要：

  Phosphonodiflourodithioacetate 2 demonstrates high reactivity towards dienes due to the presence of the two fluorine atoms. A hetero Diels-Alder reaction afforded the corresponding dihydrothiapyrans in 60-90% yields. These adducts can be submitted to a selective dihydroxylation and desulfanylation to produce phosphonodifluorothiaglycoside precursors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00204-6

文献信息

• Synthesis of thiapyranoside precursors using the building-block approach from a phosphonodifluorodithioacetate
  作者：Emmanuel Pfund、Thierry Lequeux、Michel Vazeux、Serge Masson

  DOI：10.1016/s0040-4039(02)00204-6

  日期：2002.3

  Phosphonodiflourodithioacetate 2 demonstrates high reactivity towards dienes due to the presence of the two fluorine atoms. A hetero Diels-Alder reaction afforded the corresponding dihydrothiapyrans in 60-90% yields. These adducts can be submitted to a selective dihydroxylation and desulfanylation to produce phosphonodifluorothiaglycoside precursors. (C) 2002 Elsevier Science Ltd. All rights reserved.