9-<3-O-(tert-Butyldiphenylsilyl)-5'-O-(N-phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl>-2-N-isobutyrylguanine | 166758-18-5

• 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: 9-<3-O-(tert-Butyldiphenylsilyl)-5'-O-(N-phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl>-2-N-isobutyrylguanine
• 英文别名: N-[9-[(2R,4S,5R)-4-[tert-butyl(diphenyl)silyl]oxy-5-[(1,3-dioxoisoindol-2-yl)oxymethyl]oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide
• CAS: 166758-18-5
• 化学式: C₃₈H₄₀N₆O₇Si
• 分子量: 720.857
• InChiKey: XUFSOGIFYZYADE-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  52
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  153
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-<3-O-(tert-Butyldiphenylsilyl)-5'-O-(N-phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl>-2-N-isobutyrylguanine 在 甲基肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以71%的产率得到9-<5-O-Amino-3-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-erythro-pentofuranosyl>-2-N-isobutyrylguanine
  参考文献：
  名称：

  Synthesis of 5'-O-Amino-2'-Deoxypyrimidine and Purine Nucleosides: Building-Blocks for Antisense Oligonucleotides

  摘要：

  An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcytidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.

  DOI：

  10.1021/jo00121a037
• 作为产物：
  描述：

  9-<3-O-(tert-Butyldiphenylsilyl)-5-O-(4,4'-dimethoxytrityl)-2-deoxy-β-D-erythro-pentofuranosyl>-2-N-isobutyrylguanine 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氯乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 9-<3-O-(tert-Butyldiphenylsilyl)-5'-O-(N-phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl>-2-N-isobutyrylguanine
  参考文献：
  名称：

  Synthesis of 5'-O-Amino-2'-Deoxypyrimidine and Purine Nucleosides: Building-Blocks for Antisense Oligonucleotides

  摘要：

  An efficient synthesis of 5'-O-amino-2'-deoxy analogs of uridine 1, thymidine 2, cytidine 3, 5-methylcytidine 3a, adenosine 4, and guanosine 5 was accomplished. The key step of 5'-O-N-bond formation in 2'-deoxynucleosides 1-5 was achieved via a Mitsunobu reaction in excellent yields. The 5'-O-amino nucleosides 1-5 are useful building-blocks for the synthesis of nucleoside dimers linked by a methylene(methylimino) (MMI) bridge. MMI is a novel phosphate surrogate for antisense oligonucleosides.

  DOI：

  10.1021/jo00121a037