9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-2-one

• 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-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-2-one
• 化学式: C₁₀H₁₂N₄O₅
• 分子量: 268.229
• InChiKey: PFUVWXNGEZZGDC-JXOAFFINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-2-one 在 xanthine oxidase 作用下， 生成 黄嘌呤核苷
  参考文献：
  名称：

  2'-Deoxyisoinosine: Synthesis of a Highly Fluorescent Nucleoside and Its Incorporation into Oligonucleotides

  摘要：

  The synthesis of 2'-deoxyisoinosine (2a) and the related 2',3'-dideoxynucleosides 2b and 3 is reported. The 3'-phosphonate 4b as well as the phosphoramidite 4c were prepared and employed in solid-phase oligonucleotide synthesis.

  DOI：

  10.1080/15257779508012490

文献信息

• [EN] CYTIDINE ANALOGS AND METHODS OF USE<br/>[FR] ANALOGUES DE LA CYTIDINE ET METHODES D'UTILISATION
  申请人：RIBAPHARM INC

  公开号：WO2004080466A1

  公开（公告）日：2004-09-23

  Cytidine analogs, their prodrugs and/or metabolites are employed as pharmaceutically active compounds for treatment of diseases responsive to such compounds. Particularly preferred diseases include viral diseases (e.g., HCV infection) and neoplasms.

  胞苷类似物、它们的前药和/或代谢物被用作药物活性化合物，用于治疗对这些化合物有反应的疾病。特别优选的疾病包括病毒性疾病（例如HCV感染）和肿瘤。
• High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries
  作者：Brett C. Bookser、Nicholas B. Raffaele

  DOI：10.1021/jo061885l

  日期：2007.1.1

  [GRAPHICS]The Vorbruggen glycosylation reaction was adapted into a one-step 5 min/130 degrees C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl triflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield +/- SD was 26 +/- 16%, and the average purity +/- SD was 95 +/- 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.
• 6-Chloroxanthosine, a Useful Intermediate for the Efficient Syntheses of [6-¹⁵N]-Isoguanosine, Isoinosine and Other Purine Nucleoside Analogues
  作者：L. De Napoli、A. Messere、D. Montesarchio、G. Piccialli、M. Varra

  DOI：10.1080/07328319708002532

  日期：1997.1

  6-Chloroxanthosine 1, when activated towards nucleophilic displacement at the 6-C position by conversion into the corresponding 3-N-(2,4-dinitrophenyl) derivative 4, reacted with aq. (NH3)-N-15 to afford [6-N-15]-isoguanosine 3b in 81% overall yield. Catalytic hydrogenation (Pd/C) of 1 led in 60% yield to isoinosine 8; alternatively, this could be obtained in 88% overall yield through alkaline hydrolysis of triphenylphosphonium salt 6, synthesized from 1 by reaction with PPh(3). The reactivity of 1 was further explored by treating it with primary and secondary amines: the 6-N propylamino and the 6-N piperidinyl derivatives (5a and 5b, respectively) could thus both be prepared in more than 90% yield.
• 2'-Deoxyisoinosine: Synthesis of a Highly Fluorescent Nucleoside and Its Incorporation into Oligonucleotides
  作者：Frank Seela、Yaoming Chen

  DOI：10.1080/15257779508012490

  日期：1995.5.1

  The synthesis of 2'-deoxyisoinosine (2a) and the related 2',3'-dideoxynucleosides 2b and 3 is reported. The 3'-phosphonate 4b as well as the phosphoramidite 4c were prepared and employed in solid-phase oligonucleotide synthesis.