2-[[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy]isoindole-1,3-dione

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 2-[[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy]isoindole-1,3-dione
• 化学式: C₁₇H₁₆N₄O₆
• 分子量: 372.337
• InChiKey: WPNVNISQKFLFIY-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 2'-脱氧胞嘧啶核苷 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy]isoindole-1,3-dione
  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

• US5618704A
  申请人：——

  公开号：US5618704A

  公开（公告）日：1997-04-08
• US5969118A
  申请人：——

  公开号：US5969118A

  公开（公告）日：1999-10-19
• [EN] BACKBONE MODIFIED OLIGONUCLEOTIDE ANALOGS AND PREPARATION THEREOF THROUGH RADICAL COUPLING<br/>[FR] ANALOGUES DE NUCLEOTIDES A SQUELETTE MODIFIE ET LEUR PREPARATION PAR COUPLAGE RADICALAIRE
  申请人：ISIS PHARMACEUTICALS, INC.

  公开号：WO1994022894A1

  公开（公告）日：1994-10-13

  (EN) Methods for preparing oligonucleotide analogs which have improved nuclease resistance and improved cellular uptake are provided. In preferred embodiments, the methods involve radical coupling of 3'- and 5'- substituted or 5'- and 3'-substituted nucleosidic synthons.(FR) L'invention concerne des procédés de préparation d'analogues de nucléotides présentant une résistance accrue à la nucléase et une meilleure fixation cellulaire. Dans les modes préférés de réalisation, les procédés comprennent le couplage de synthons nucléosidiques à substitution 3' et 5' ou 5' et 3'.
• 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.