2-N,5'-O-diacetylguanosine | 53766-79-3

• 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: 2-N,5'-O-diacetylguanosine
• 英文别名: N²,O^5'-diacetyl-guanosine；N²,O⁵'-Diacetylguanosin；[(2R,3S,4R,5R)-5-(2-acetamido-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl acetate
• CAS: 53766-79-3
• 化学式: C₁₄H₁₇N₅O₇
• 分子量: 367.318
• InChiKey: XDPCQQBTZOMFPX-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  164
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester 在 正丁基锂 、 2,2,2-三氟乙醇 作用下， 以 正己烷 为溶剂， 反应 1.5h， 以84%的产率得到2-N,5'-O-diacetylguanosine
  参考文献：
  名称：

  Selective Removal of the 2‘- and 3‘-O-Acyl Groups from 2‘,3‘,5‘-Tri-O-acylribonucleoside Derivatives with Lithium Trifluoroethoxide¹

  摘要：

  Selective cleavage of O2' and O3' ester groups from ribonucleoside derivatives has been accomplished with Dowex 1 x 2 (CF3CH2O-) in 2,2,2-trifluoroethanol (TFE) or lithium trifluoroethoxide/TFE. Deacylations with Li+ -OCH2CF3/TFE proceed at ambient temperature (or with mild heating) to give the 5'-O-acyl derivatives in superior yields and higher purity than prior approaches for selective O2' and O3' ester deprotection.

  DOI：

  10.1021/jo0600104

文献信息

• Ishido, Yoshiharu; Sakairi, Nobuo; Okazaki, Kei, Journal of the Chemical Society. Perkin transactions I, 1980, p. 563 - 573
  作者：Ishido, Yoshiharu、Sakairi, Nobuo、Okazaki, Kei、Nakazaki, Nobuo

  DOI：——

  日期：——
• PHOSPHORAMIDITES FOR SYNTHETIC RNA IN THE REVERSE DIRECTION, EFFICIENT RNA SYNTHESIS AND CONVENIENT INTRODUCTION OF 3'-END LIGANDS, CHROMOPHORES AND MODIFICATIONS OF SYNTHETIC RNA
  申请人：Srivastava Suresh C.

  公开号：US20110137010A1

  公开（公告）日：2011-06-09

  The present invention provides building blocks and methods for synthesizing very pure RNA in a form that can efficiently be modified at the 3′ end. Reverse RNA monomer phosphoramidites have been developed for RNA synthesis in 5′→3′ direction, leading to very clean oligo synthesis that allows for the introduction of various modifications at the 3′-end cleanly and efficiently. Higher coupling efficiency per step have been observed during automated oligo synthesis with the reverse RNA amidites disclosed herein, resulting in a greater ability to achieve higher purity and produce very long oligonucleotides. The use of the reverse RNA phosphoramidites in the synthetic process of this invention leads to oligonucleotides free of N+1 species.
• [EN] PHOSPHORAMIDITES FOR SYNTHETIC RNA IN THE REVERSE DIRECTION<br/>[FR] PHOSPHORAMIDITES POUR ARN SYNTHÉTIQUE EN SENS INVERSE
  申请人：CHEMGENES CORP

  公开号：WO2011103468A2

  公开（公告）日：2011-08-25

  The present invention provides building blocks and methods for synthesizing very pure RNA in a form that can efficiently be modified at the 3' end. Reverse RNA monomer phosphoramidites have been developed for RNA synthesis in 5'-> 3' direction, leading to very clean oligo synthesis that allows for the introduction of various modifications at the 3 '-end cleanly and efficiently. Higher coupling efficiency per step have been observed during automated oligo synthesis with the reverse RNA amidites disclosed herein, resulting in a greater ability to achieve higher purity and produce very long oligonucleotides. The use of the reverse RNA phosphoramidites in the synthetic process of this invention leads to oligonucleotides free of N+1 species.