2',5'-bis-O-(tert-butyldimethylsilyl)-2-N-<2-<(tert-butyldiphenylsiloxy)methyl>benzoyl>guanosine | 143294-21-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2',5'-bis-O-(tert-butyldimethylsilyl)-2-N-<2-<(tert-butyldiphenylsiloxy)methyl>benzoyl>guanosine
• 英文别名: N-[9-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-[[tert-butyl(diphenyl)silyl]oxymethyl]benzamide
• CAS: 143294-21-7
• 化学式: C₄₆H₆₅N₅O₇Si₃
• 分子量: 884.308
• InChiKey: UHMBWWOTRNZJNP-GNECSJIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.12
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2',5'-bis-O-(tert-butyldimethylsilyl)-2-N-<2-<(tert-butyldiphenylsiloxy)methyl>benzoyl>guanosine 、 2',3'-bis-O-(tert-butyldimethylsilyl)uridin-5'-yl hydrogen phosphonate,triethylammonium salt 在 三甲基乙酰氯 作用下， 以 吡啶 为溶剂， 以42%的产率得到2',5'-bis-O-(tert-butyldimethylsilyl)-2-N-<2-<(tert-butyldiphenylsiloxy)methyl>benzoyl>guanosin-3'-yl 2',3'-bis-O-(tert-butyldimethylsilyl)uridin-5'-yl hydrogen phosphonate
  参考文献：
  名称：

  Synthesis of diribonucleoside phosphorothioates via stereospecific sulfuration of H-phosphonate diesters

  摘要：

  Sulfurization of diribonucleoside H-phosphonates with elemental sulfur was found to be a stereospecific reaction. With this finding as the basis, an efficient method for the preparation of stereochemically homogeneous diribonucleoside phosphorothioates has been developed. The procedure consists of the synthesis and separation of the diastereomeric (R(p) and S(p)) pairs of the corresponding H-phosphonate diesters, followed by their stereospecific sulfurization and a single deprotection step using fluoride ion. The methodology has been used in synthesis of eight diribonucleoside phosphorothioates (four pairs of R(p) and S(p) diastereomers).

  DOI：

  10.1021/jo00049a022
• 作为产物：
  描述：

  鸟苷 在 吡啶 、 silver nitrate 作用下， 以 四氢呋喃 为溶剂， 生成 2',5'-bis-O-(tert-butyldimethylsilyl)-2-N-<2-<(tert-butyldiphenylsiloxy)methyl>benzoyl>guanosine
  参考文献：
  名称：

  Synthesis of diribonucleoside phosphorothioates via stereospecific sulfuration of H-phosphonate diesters

  摘要：

  Sulfurization of diribonucleoside H-phosphonates with elemental sulfur was found to be a stereospecific reaction. With this finding as the basis, an efficient method for the preparation of stereochemically homogeneous diribonucleoside phosphorothioates has been developed. The procedure consists of the synthesis and separation of the diastereomeric (R(p) and S(p)) pairs of the corresponding H-phosphonate diesters, followed by their stereospecific sulfurization and a single deprotection step using fluoride ion. The methodology has been used in synthesis of eight diribonucleoside phosphorothioates (four pairs of R(p) and S(p) diastereomers).

  DOI：

  10.1021/jo00049a022

文献信息

• Synthesis of diribonucleoside phosphorothioates via stereospecific sulfuration of H-phosphonate diesters
  作者：H. Almer、J. Stawinski、R. Stroemberg、M. Thelin

  DOI：10.1021/jo00049a022

  日期：1992.11

  Sulfurization of diribonucleoside H-phosphonates with elemental sulfur was found to be a stereospecific reaction. With this finding as the basis, an efficient method for the preparation of stereochemically homogeneous diribonucleoside phosphorothioates has been developed. The procedure consists of the synthesis and separation of the diastereomeric (R(p) and S(p)) pairs of the corresponding H-phosphonate diesters, followed by their stereospecific sulfurization and a single deprotection step using fluoride ion. The methodology has been used in synthesis of eight diribonucleoside phosphorothioates (four pairs of R(p) and S(p) diastereomers).