3-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-phenyl-8-(2,2,6,6-tetramethyl-piperidin-1-yl)-3H-7-oxa-1,3,4,5,8a-pentaaza-8-phospha-cyclopenta[b]naphthalen-9-one | 145744-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-phenyl-8-(2,2,6,6-tetramethyl-piperidin-1-yl)-3H-7-oxa-1,3,4,5,8a-pentaaza-8-phospha-cyclopenta[b]naphthalen-9-one
• CAS: 145744-03-2
• 化学式: C₄₄H₇₅N₆O₆PSi₃
• 分子量: 899.346
• InChiKey: VNDXYSJAODSWBZ-KYIAHQGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.52
• 重原子数：
  60.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  114.46
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  N2-Benzoyl-2',3',5'-tri-O-TBDMS-β-D-ribofuranosyl-guanosine 、 2,2,6,6-tetramethylpiperidinodichlorophosphine 在 N,N-二异丙基乙胺 作用下， 以48%的产率得到3-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-phenyl-8-(2,2,6,6-tetramethyl-piperidin-1-yl)-3H-7-oxa-1,3,4,5,8a-pentaaza-8-phospha-cyclopenta[b]naphthalen-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