6-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1-[di(propan-2-yl)amino]-3-phenyl-[1,3,5,2]oxadiazaphosphinino[3,4-a]purin-9-one | 103457-17-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 6-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1-[di(propan-2-yl)amino]-3-phenyl-[1,3,5,2]oxadiazaphosphinino[3,4-a]purin-9-one
• CAS: 103457-17-6
• 化学式: C₄₁H₇₁N₆O₆PSi₃
• 分子量: 859.282
• InChiKey: NMPQXRFYKXKBFF-PWSHPZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  57
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1-[di(propan-2-yl)amino]-3-phenyl-[1,3,5,2]oxadiazaphosphinino[3,4-a]purin-9-one 在 叔丁基过氧化氢 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以98%的产率得到6-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1-[di(propan-2-yl)amino]-1-oxo-3-phenyl-[1,3,5,2]oxadiazaphosphinino[3,4-a]purin-9-one
  参考文献：
  名称：

  Tricyclic “oxadiazaphosphorine oxide” guanosines: A new strategy to the protection of guanine bases during RNA synthesis

  摘要：

  A novel strategy for simultaneously protecting the lactam and N2-amino functions of guanine nucleosides is reported. N2-benzoylated guanosines were readily converted into tricyclic "oxadiazaphosphorine oxide" guanosines upon reaction with N,N-diisopropylphosphoramidous dichloride followed by oxidation with t-butyl hydroperoxide. The tricyclic guanine derivative is reconverted readily to the natural guanine aglycone upon treatment with ethylenediamine/ethanol (1:4, 1 min, r.t.).

  DOI：

  10.1016/s0040-4039(00)61764-1
• 作为产物：
  描述：

  N2-Benzoyl-2',3',5'-tri-O-TBDMS-β-D-ribofuranosyl-guanosine 、 二氯-N,N-二异丙基亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 氯仿 为溶剂， 反应 0.33h， 以96%的产率得到6-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1-[di(propan-2-yl)amino]-3-phenyl-[1,3,5,2]oxadiazaphosphinino[3,4-a]purin-9-one
  参考文献：
  名称：

  Modification of guanine bases: reaction of N2-acylated guanine nucleosides with dichloro-(N,N-diisopropylamino)phosphine

  摘要：

  DOI：

  10.1021/jo00368a037

文献信息

• Tricyclic “oxadiazaphosphorine oxide” guanosines: A new strategy to the protection of guanine bases during RNA synthesis
  作者：Masad J. Damha、Yunkui Guo、Steve V. Zabarylo、Kanjana Ganeshan、Paul A. Giannaris

  DOI：10.1016/s0040-4039(00)61764-1

  日期：1992.11

  A novel strategy for simultaneously protecting the lactam and N2-amino functions of guanine nucleosides is reported. N2-benzoylated guanosines were readily converted into tricyclic "oxadiazaphosphorine oxide" guanosines upon reaction with N,N-diisopropylphosphoramidous dichloride followed by oxidation with t-butyl hydroperoxide. The tricyclic guanine derivative is reconverted readily to the natural guanine aglycone upon treatment with ethylenediamine/ethanol (1:4, 1 min, r.t.).
• Modification of guanine bases: reaction of N2-acylated guanine nucleosides with dichloro-(N,N-diisopropylamino)phosphine
  作者：Masad J. Damha、Kelvin K. Ogilvie

  DOI：10.1021/jo00368a037

  日期：1986.9