9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine | 166758-20-9

• 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-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine
• 英文别名: 2'-Deoxy-O6-diphenylcarbamoyl-N2-isobutyryl-5'-O-phthalimidoguanosine；[9-[(2R,4S,5R)-5-[(1,3-dioxoisoindol-2-yl)oxymethyl]-4-hydroxyoxolan-2-yl]-2-(2-methylpropanoylamino)purin-6-yl] N,N-diphenylcarbamate
• CAS: 166758-20-9
• 化学式: C₃₅H₃₁N₇O₈
• 分子量: 677.673
• InChiKey: RGBHRXTUPJOOLN-OYUWMTPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  178
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-2-N-isobutyrylguanine 在 氨 、 甲基肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 5'-O-Amino-2'-deoxyguanosine
  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：

  二苯氨基甲酰氯 在 吡啶 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 9-(5-O-(N-Phthalimidyl)-2-deoxy-β-D-erythro-pentofuranosyl)-6-O-(diphenylcarbamoyl)-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

文献信息

• Backbone modified oligonucleotide analogs and solid phase synthesis
  申请人：ISIS Pharmaceuticals, Inc.

  公开号：US05541307A1

  公开（公告）日：1996-07-30

  Compounds and methods for preparing oligonucleotide analogs are provided. In preferred embodiments, the methods involve solid-phase coupling of synthons bearing either 3'-electrophillic groups and 5'-nucleophilic groups or 5'-electrophillic groups and 3'-nucleophilic groups to form neutral, achiral oligomers.

  提供了制备寡核苷酸类似物的化合物和方法。在首选实施例中，所述方法涉及固相偶联具有3'-亲电基团和5'-亲核基团或5'-亲电基团和3'-亲核基团的合成物，以形成中性，无手性的寡聚物。
• US5541307A
  申请人：——

  公开号：US5541307A

  公开（公告）日：1996-07-30
• Synthesis of 5'-O-Amino-2'-Deoxypyrimidine and Purine Nucleosides: Building-Blocks for Antisense Oligonucleotides
  作者：Michel Perbost、Tomonori Hoshiko、Francois Morvan、Eric Swayze、Richard H. Griffey、Yogesh S. Sanghvi

  DOI：10.1021/jo00121a037

  日期：1995.8

  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.