O-cholesteryl (O-tert-butyl) thiophosphorofluoridate | 404951-93-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: O-cholesteryl (O-tert-butyl) thiophosphorofluoridate
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-fluoro-[(2-methylpropan-2-yl)oxy]-sulfanylidene-lambda5-phosphane；[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-fluoro-[(2-methylpropan-2-yl)oxy]-sulfanylidene-λ5-phosphane
• CAS: 404951-93-5
• 化学式: C₃₁H₅₄FO₂PS
• 分子量: 540.807
• InChiKey: LMEIPOKAAYHVCA-LASBQPCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-cholesteryl (O-tert-butyl) thiophosphorofluoridate 以 乙腈 为溶剂， 反应 2.0h， 以96%的产率得到O-cholesteryl thiophosphoromonofluoridate
  参考文献：
  名称：

  Synthesis of phosphorofluoridates and phosphorofluoridothioates via the phosphoramidite approach

  摘要：

  我们介绍了一种非常高效的合成方法，能够制备出磷氟酸盐RO-P(O)(OH)F 1或磷氟硫酸盐RO-P(S)(OH)F 2，其方法基于氟磷酰胺中间体(RO)P(F)NiPr25 [R = 9-(羟乙氧甲基)鸟嘌呤基、3′叠氮-3′脱氧胸苷基、胸苷基、脱水胸苷基、胆固醇基、N6-苯甲酰-5′-O-(4,4′-二甲氧基三苯甲基)-2′-脱氧腺苷基]。氨基的活化采用三甲基氯硅烷（TMCS）完成。

  DOI：

  10.1039/b413552k
• 作为产物：
  描述：

  O-cholesteryl O-(4-nitrophenyl) N,N-diisopropylphosphoramidite 在 三甲基氯硅烷 、 (C₃H₇)2NH 、 四丁基氟化铵 、 sulfur 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 生成 O-cholesteryl (O-tert-butyl) thiophosphorofluoridate
  参考文献：
  名称：

  Synthesis of phosphorofluoridates and phosphorofluoridothioates via the phosphoramidite approach

  摘要：

  我们介绍了一种非常高效的合成方法，能够制备出磷氟酸盐RO-P(O)(OH)F 1或磷氟硫酸盐RO-P(S)(OH)F 2，其方法基于氟磷酰胺中间体(RO)P(F)NiPr25 [R = 9-(羟乙氧甲基)鸟嘌呤基、3′叠氮-3′脱氧胸苷基、胸苷基、脱水胸苷基、胆固醇基、N6-苯甲酰-5′-O-(4,4′-二甲氧基三苯甲基)-2′-脱氧腺苷基]。氨基的活化采用三甲基氯硅烷（TMCS）完成。

  DOI：

  10.1039/b413552k

文献信息

• Novel phosphitylating reagents containing a phosphorus–fluorine bond and their application in efficient synthesis of phosphorofluoridates and phosphorofluoridothionates
  作者：Wojciech Dąbkowski、Izabela Tworowska

  DOI：10.1039/b103082p

  日期：——

  Novel phosphitylating reagents containing a P–F bond are obtained in excellent yield from commercial materials. They react with alcohols at 20 °C in neutral solvents in the presence of tetrazole, chlorotrimethylsilane or benzoyl chloride to give the intermediate phosphorofluoridites. Subsequent oxidation or sulfurization followed by the removal of protecting groups gives the phosphorofluoridates and thiophosphorofluoridates in over 90% total yield.

  包含 P–F 键的新型磷酸化试剂以优异的产率从商业原料中获得。它们在四唑、氯三甲基硅烷或苯甲酰氯的存在下，在中性溶剂中于 20 °C 下与醇反应，生成中间体氟磷酸酯。随后的氧化或硫化处理及保护基团的去除，可得到总产率超过 90% 的氟磷酸酯和硫氟磷酸酯。
• New Phosphitylating Reagents Containing P-F Bond and Their Application in the Synthesis of P-Fluoro Nucleosidyl Phosphates, Thiophosphates and Selenophosphates
  作者：W. Dąbkowski、I. Tworowska、E. Poniatowska、J. Michalski、F. Cramer

  DOI：10.1080/07328319908044679

  日期：1999.6

  An efficient and general synthesis of phosphorofluoridates RO-P(X)(OH)F (X=O) and their analogues (X=S, Se) based on two new phosphitylating reagents: 2-cyanoethyl-N,N-diisopropylfluorophosphoioamidite F-P(NPr2i)OCH2CH2CN and tertbutyl-N,N-diisopropylfluorophosphoroamidite F-P(NPr2i)OBut is described.
• Synthesis of phosphorofluoridates and phosphorofluoridothioates via the phosphoramidite approach
  作者：Wojciech Dabkowski、Izabela Tworowska

  DOI：10.1039/b413552k

  日期：——

  We present a very efficient synthetic procedure leading to the phosphorofluoridates RO-P(O)(OH)F 1 or phosphorofluoridothioates RO-P(S)(OH)F 2, which is based on the intermediary of fluorophosphoramidites (RO)P(F)NiPr25 [R = 9-(hydroxyethyloxymethyl)guaninyl), 3′azido-3′deoxythymidinyl, thymidinyl, anhydrothymidinyl, cholesteryl, N6-benzoyl-5′-O-(4,4′-dimethoxytrityl)-2′-deoxyadenosinyl]. The activation of the amino group was performed with trimethylchlorosilane (TMCS).

  我们介绍了一种非常高效的合成方法，能够制备出磷氟酸盐RO-P(O)(OH)F 1或磷氟硫酸盐RO-P(S)(OH)F 2，其方法基于氟磷酰胺中间体(RO)P(F)NiPr25 [R = 9-(羟乙氧甲基)鸟嘌呤基、3′叠氮-3′脱氧胸苷基、胸苷基、脱水胸苷基、胆固醇基、N6-苯甲酰-5′-O-(4,4′-二甲氧基三苯甲基)-2′-脱氧腺苷基]。氨基的活化采用三甲基氯硅烷（TMCS）完成。