9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-(2-propylimidazol-1-yl)purine | 917224-85-2

• 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-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-(2-propylimidazol-1-yl)purine
• 英文别名: 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-2-amino-6-(2-propylimidazol-1-yl)purine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[2-amino-6-(2-propylimidazol-1-yl)purin-9-yl]oxolan-2-yl]methyl acetate
• CAS: 917224-85-2
• 化学式: C₂₂H₂₇N₇O₇
• 分子量: 501.499
• InChiKey: UUCBLLPUEZXLCF-HAXDFEGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  176
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-(2-propylimidazol-1-yl)purine 在 三甲基氯硅烷 、 亚硝酸苄基三乙基铵 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-chloro-6-(2-propylimidazol-1-yl)purine
  参考文献：
  名称：

  Structure and Synthesis of 6-(Substituted-imidazol-1-yl)purines:  Versatile Substrates for Regiospecific Alkylation and Glycosylation at N9¹

  摘要：

  X-ray crystal structures of several 6-(azolyl) purine base and nucleoside derivatives show essentially coplanar conformations of the purine and appended 6-(azolyl) rings. However, the planes of the purine and imidazole rings are twisted similar to 57 degrees in a 2-chloro-6-(4,5-diphenylimidazol-1-yl) purine nucleoside, and a twist angle of similar to 61 degrees was measured between the planes of the purine and pyrrole rings in the structure of a 6-(2,5-dimethylpyrrol-1-yl) purine nucleoside derivative. Shielding "above" N7 of the purine ring by a proximal C-H on the 6-azolyl moiety is apparent with the coplanar compounds, but this effect is diminished in those without coplanarity. Syntheses of 6-(azolyl)purines from both base and nucleoside starting materials are described. Treatment of 2,6- dichloropurine with imidazole gave 2-chloro-6-(imidazol)-yl)purine. Modified Appel reactions at C6 of trityl-protected hypoxanthine and guanine derivatives followed by detritylation gave 6-(imidazol-1-yl)- and 2-amino-6-(imidazol-1-yl) purines. Imidazole was introduced at C6 of 2',3',5'-tri-O-acetylinosine by a modified Appel reaction, and solvolysis of the glycosyl linkage gave 6-(imidazol-1-yl) purine. Guanosine triacetate was transformed into the protected 2,6-dichloropurine nucleoside, which was subjected to SNAr displacement with imidazoles at C6 followed by glycosyl solvolysis to provide 2-chloro-6-(substituted-imidazol-1-yl) purines. Potential applications of these purine derivatives are outlined.

  DOI：

  10.1021/jo060340o
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-amino-6-(2-propylimidazol-1-yl)purine
  参考文献：
  名称：

  WO2006/138396

  摘要：

  公开号：

文献信息

• Methods For Selective N-9 Glycosylation of Purines
  申请人：Robins Morris J.

  公开号：US20080207891A1

  公开（公告）日：2008-08-28

  A process for providing regiospecific and highly stereoselective synthesis of 9-β anomeric purine nucleoside analogs is described. The introduction of the sugar moiety on to 6-(azolyl)-substituted purine bases is performed so that highly stereoselective formation of the β anomers of only the 9 position regioisomers of the purine nucleoside analogs (either D or L enantiomers) is obtained. This regiospecific and stereoselective introduction of the sugar moiety allows the synthesis of nucleoside analogs, and in particular 2′-deoxy, 3′-deoxy, 2′-deoxy-2′-halo-arabino and 2′,3′-dideoxy-2′-halo-threo purine nucleoside analogs, in high yields without formation of the 7-positional regioisomers. Processes for providing novel 6-(azolyl)purines for the regiospecific and highly stereoselective synthesis of 9-β anomeric purine nucleoside analogs are described. The compounds are drugs or intermediates to drugs.

  本文描述了一种提供9-β异构嘌呤核苷类似物的区域特异性和高度立体选择性合成的方法。将糖基引入到6-(咪唑基)-取代的嘌呤碱基上，以获得嘌呤核苷类似物的β异构体的高度立体选择性形成（D或L对映体）。这种区域特异性和立体选择性引入糖基的方法，允许高产率地合成核苷类似物，特别是2'-去氧、3'-去氧、2'-去氧-2'-卤代阿拉伯糖和2',3'-二去氧-2'-卤代-threo嘌呤核苷类似物，而不形成7位异构体。本文还描述了提供新型6-(咪唑基)嘌呤用于区域特异性和高度立体选择性合成9-β异构嘌呤核苷类似物的方法。这些化合物是药物或药物中间体。
• Methods for selective N-9 glycosylation of purines
  申请人：Brigham Young University

  公开号：US07855285B2

  公开（公告）日：2010-12-21

  A process for providing regiospecific and highly stereoselective synthesis of 9-β anomeric purine nucleoside analogs is described. The introduction of the sugar moiety on to 6-(azolyl)-substituted purine bases is performed so that highly stereoselective formation of the β anomers of only the 9 position regioisomers of the purine nucleoside analogs (either D or L enantiomers) is obtained. This regiospecific and stereoselective introduction of the sugar moiety allows the synthesis of nucleoside analogs, and in particular 2′-deoxy, 3′-deoxy, 2′-deoxy-2′-halo-arabino and 2′,3′-dideoxy-2′-halo-threo purine nucleoside analogs, in high yields without formation of the 7-positional regioisomers. Processes for providing novel 6-(azolyl)purines for the regiospecific and highly stereoselective synthesis of 9-β anomeric purine nucleoside analogs are described. The compounds are drugs or intermediates to drugs.

  本文描述了一种提供9-β异构嘌呤核苷类似物的区域特异性和高度立体选择性合成的过程。将糖基引入到6-(唑基)-取代的嘌呤碱基上，以获得仅嘌呤核苷类似物的9位区异构体（D或L对映体）的β异构体的高度立体选择性形成。这种区域特异性和立体选择性的糖基引入允许合成核苷类似物，特别是高产率地合成2'-去氧、3'-去氧、2'-去氧-2'-卤代阿拉伯糖和2',3'-二去氧-2'-卤代-葡萄糖嘌呤核苷类似物，而不形成7位区异构体。本文还描述了提供新型6-(唑基)嘌呤用于区域特异性和高度立体选择性合成9-β异构嘌呤核苷类似物的过程。这些化合物是药物或药物中间体。
• METHODS FOR SELECTIVE N-9 GLYCOSYLATION OF PURINES
  申请人：Brigham Young University

  公开号：EP1895841A2

  公开（公告）日：2008-03-12
• US7855285B2
  申请人：——

  公开号：US7855285B2

  公开（公告）日：2010-12-21
• [EN] METHODS FOR SELECTIVE N-9 GLYCOSYLATION OF PURINES<br/>[FR] PROCEDES DE N-9 GLYCOSYLATION SELECTIVE DE PURINES
  申请人：BRIGHAM YOUNG UNIVERSITY TRANS

  公开号：WO2006138396A2

  公开（公告）日：2006-12-28

  [EN] A process for providing regiospecific and highly stereoselective synthesis of 9-ß anomeric purine nucleoside analogs is described. The introduction of the sugar moiety on to 6-(azolyl)-substituted purine bases is performed so that highly stereoselective formation of the ß anomers of only the 9 position regioisomers of the purine nucleoside analogs (either D or L enantiomers) is obtained. This regiospecific and stereoselective introduction of the sugar moiety allows the synthesis of nucleoside analogs, and in particular 2'-deoxy, 3'-deoxy, 2'-deoxy-2'-halo-arabino and 2',3'-dideoxy-2'-halo-threo purine nucleoside analogs, in high yields without formation of the 7-positional regioisomers. Processes for providing novel 6-(azolyl)purines for the regiospecific and highly stereoselective synthesis of 9-ß anomeric purine nucleoside analogs are described. The compounds are drugs or intermediates to drugs.
  [FR] L'invention concerne un procédé permettant d'obtenir une synthèse régiospécifique et hautement stéréosélective d'analogues de nucléosides de purines anomériques 9-ß. L'introduction de la fraction de sucre sur des bases de purines 6-(azolyl)-substituées est effectuée de manière qu'une formation hautement stéréosélective des anomères ß d'uniquement les régiosomères en position 9 des analogues de nucléosides de purines (soit des enantiomères D ou L) soit obtenue. Cette introduction régiospécifique et stéréosélective de la fraction de sucre permet d'obtenir la synthèse des analogues de nucléosides, notamment des analogues de nucléosides de purines 2'-désoxy, 3'-désoxy, 2'-désoxy-2'-halo-arabino et 2',3'-didésoxy-2'-halo-thréo, à des rendements élevés sans formation des régiosiomères en position 7. L'invention concerne également des procédés permettant de préparer des purines 6-(azolyl) destinées à la synthèse régiospécifique et hautement stéréosélective d'analogues de nucléosides de purines anomériques 9-ß. Les composés sont des médicaments ou des intermédiaires aux médicaments.