1-(5-O-Acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine | 62805-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1-(5-O-Acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine
• 英文别名: 9-(5-acetoxymethyl-2,5-dihydro-furan-2-yl)-9H-purin-6-ylamine；((2S,5R)-5-(6-Amino-9H-purin-9-yl)-2,5-dihydrofuran-2-yl)methyl acetate；[(2S,5R)-5-(6-aminopurin-9-yl)-2,5-dihydrofuran-2-yl]methyl acetate
• CAS: 62805-50-9
• 化学式: C₁₂H₁₃N₅O₃
• 分子量: 275.267
• InChiKey: IFKCAUAEVYDRHY-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(5-O-Acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine 在 氨 作用下， 以 甲醇 为溶剂， 以85%的产率得到2,3-二脱氧-2,3-二氢腺苷
  参考文献：
  名称：

  An Efficient and General Synthesis of 5′-Esters of 2′,3′-Didehydro-2′,3′-dideoxynucleosides: A Facile Opening of 2′,3′-Orthoacetates of Ribonucleosides Followed by Reductive Elimination of the Halogenoacetates

  摘要：

  描述了一种从核糖核苷开始的三步反应序列，最终得到相应的5'-O-酰基-2',3'-二脱氧-2',3'-二氢核苷。关键中间体是溴乙酸酯，由2',3'-甲氧基亚乙基核苷与乙酰溴反应制得。利用锌-铜偶对溴乙酸酯进行还原消除，可在良好的总体产率下获得目标化合物。

  DOI：

  10.1055/s-1993-25853
• 作为产物：
  描述：

  2',3'-O-Methoxy-ethyliden-adenosin 在 铜 、 锌 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 1-(5-O-Acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine
  参考文献：
  名称：

  An Efficient and General Synthesis of 5′-Esters of 2′,3′-Didehydro-2′,3′-dideoxynucleosides: A Facile Opening of 2′,3′-Orthoacetates of Ribonucleosides Followed by Reductive Elimination of the Halogenoacetates

  摘要：

  描述了一种从核糖核苷开始的三步反应序列，最终得到相应的5'-O-酰基-2',3'-二脱氧-2',3'-二氢核苷。关键中间体是溴乙酸酯，由2',3'-甲氧基亚乙基核苷与乙酰溴反应制得。利用锌-铜偶对溴乙酸酯进行还原消除，可在良好的总体产率下获得目标化合物。

  DOI：

  10.1055/s-1993-25853

文献信息

• Novel method for the synthesis of 2',3'-unsaturated nucleosides from 2'(3')-acetoxy-3'(2')-halogeno derivatives by using sodium dithionite with viologen as a reductive elimination mediator.
  作者：Yusuke AMINO、Hisao IWAGAMI

  DOI：10.1248/cpb.39.622

  日期：——

  Reductive elimination of vicinal acetylated halohydrins with Na2S2O4 as the reducing agent and viologen as the reduction mediator in a two-phase water-organic system is described. 2', 3'-Unsaturated nucleosides such as 1-(5-O-acetyl-2, 3-dideoxy-β-D-glycero-pent-2-enofuranosyl)adenine, -hypoxanthine and uracil were obtained from 2'(3')-acetoxy-3'(2')-halogeno derivatives in good yields by meanes of this procedure.

  描述了以 Na2S2O4 为还原剂、紫胶烯为还原介质，在两相水-有机体系中对邻位乙酰化卤素进行还原消除的过程。通过这种方法，从 2'(3')-乙酰氧基-3'(2')-卤代衍生物中获得了 2'、3'-不饱和核苷，如 1-(5-O-乙酰基-2, 3-二脱氧-β-D-甘油-2-戊烯呋喃糖基)腺嘌呤、次黄嘌呤和尿嘧啶，收率很高。
• Process for the production of purine nucleoside compounds
  申请人：Torii Takayoshi

  公开号：US20050171126A1

  公开（公告）日：2005-08-04

  2′,3′-didehydro-2′,3′-dideoxypurine nucleoside compounds and 2′,3′-dideoxypurine nucleoside compounds may be produced efficiently by treating a 3′-deoxy-3′-bromopurine nucleoside compound with a perfluoroalkanesulfonyl fluoride in the presence of a base to give a 2′,3′-didehydro-2′,3′-dideoxypurine nucleoside compound, which may be converted to a 2′,3′-dideoxypurine nucleoside compound, by catalytic hydrogenation.

  2′,3′-二去氢-2′,3′-二脱氧嘌呤核苷化合物和2′,3′-二脱氧嘌呤核苷化合物可以通过在碱的存在下用全氟烷磺酰氟处理3′-脱氧-3′-溴嘌呤核苷化合物来高效制备，从而得到2′,3′-二去氢-2′,3′-二脱氧嘌呤核苷化合物，通过催化氢化可以将其转化为2′,3′-二脱氧嘌呤核苷化合物。
• Process for preparing 2',3'-dideoxy nucleoside derivatives
  申请人：Ajinomoto Co., Inc.

  公开号：US05106962A1

  公开（公告）日：1992-04-21

  A process for preparing 2',3'-didehydro-2',3'-dideoxynucleoside derivatives (III) ##STR1## by reacting a compound (I) ##STR2## with a viologen (N,N'-dialkyl-4,4'-bipyridinium salt) is disclosed. In the formulae R.sup.1 is C.sub.1-12 acyl or sulfonyl, R.sup.2 is hydrogen, C.sub.1-12 acyl, C.sub.1-12 alkyl, C.sub.6-18 aralkyl, or silyl, X is a halogen atom, and B is a purine, pyrimidine, imidazole, or triazole base residue.

  揭示了一种制备2'，3'-二去氢-2'，3'-二脱氧核苷衍生物（III）的过程，该过程通过将化合物（I）与维奥洛根（N，N'-二烷基-4,4'-联吡啶盐）反应而得到。在公式中，R1是C1-12酰基或磺酰基，R2是氢，C1-12酰基，C1-12烷基，C6-18芳基烷基或硅基，X是卤素原子，B是嘌呤，嘧啶，咪唑或三唑碱基残基。
• A process for the production of purine nucleoside compounds
  申请人：Ajinomoto Co., Inc.

  公开号：EP1550665A1

  公开（公告）日：2005-07-06

  The invention provides a process wherein a 3'-deoxy-3'-halopurine nucleoside compound is treated with perfluoroalkanesulfonyl fluoride in the presence of a base to give a 2',3'-didehydro-2',3'-dideoxypurine nucleoside compound. The resulting compound may be subjected to a catalytic hydrogenolysis to obtain a 2',3'-dideoxypurine nucleoside compound.

  本发明提供了一种方法，其中将3'-去氧-3'-卤代嘌呤核苷化合物在碱存在下与全氟烷基磺酰氟进行处理，以得到2',3'-双脱氢-2',3'-双去氧嘌呤核苷化合物。所得化合物可以经过催化氢解作用，得到2',3'-双去氧嘌呤核苷化合物。
• CONVENIENT SYNTHESIS OF FLUORINATED NUCLEOSIDES WITH PERFLUOROALKANESULFONYL FLUORIDES
  作者：Satoshi Takamatsu、Satoshi Katayama、Naoko Hirose、Etienne De Cock、Geert Schelkens、Marc Demillequand、Jozef Brepoels、Kunisuke Izawa

  DOI：10.1081/ncn-120016572

  日期：2002.12.31

  Perfluoroalkanesulfonyl fluorides are effective dehydroxy-fluorination agents for the hydroxyl group at the sugar moiety of nucleoside derivatives and give the corresponding fluorinated nucleosides in good yield with an inversion of configuration in a single step.