2-N-acetyl-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-O-(diphenylcarbamoyl)guanine | 112233-75-7

• 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-acetyl-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-O-(diphenylcarbamoyl)guanine
• 英文别名: 2-(acetylamino)-6-(diphenylcarbamoyloxy)-9-(β-D-tri-O-acetylribofuranosyl)-9H-purine；N-Acetyl-guanosine2',3',5'-Triacetate6-(N,N-Diphenylcarbamate)；[(2R,3R,4R,5R)-5-[2-acetamido-6-(diphenylcarbamoyloxy)purin-9-yl]-3,4-diacetyloxyoxolan-2-yl]methyl acetate
• CAS: 112233-75-7
• 化学式: C₃₁H₃₀N₆O₁₀
• 分子量: 646.613
• InChiKey: XSSWDMURTPAIDU-CTDWIVFPSA-N

物化性质

• 密度：
  1.45±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿、二氯甲烷

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  190
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-N-acetyl-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-O-(diphenylcarbamoyl)guanine 在 三氟乙酸 作用下， 反应 0.25h， 以96%的产率得到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
  参考文献：
  名称：

  Selective cleavage of the O6-diphenylcarbamoyl group from sugar-modified guanosines for incorporation into oligo-RNA

  摘要：

  A facile conversion of 2',3',5'-O-tri-(Bz, Tol or Ac)-N-2-(Ac or iBu)-O-6-DPC-guanosine to N-2-(Ac or iBu)guanosine has been achieved in 89-98% yield by short treatment with 90% aqueous TFA for smooth cleavage of the DPC group followed by treatment with sodium ethoxide in pyridine-ethanol mixture at room temperature. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01524-5
• 作为产物：
  描述：

  二苯氨基甲酰氯 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 、 N,N-二异丙基乙胺 作用下， 以 吡啶 为溶剂， 反应 2.25h， 生成 2-N-acetyl-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-O-(diphenylcarbamoyl)guanine
  参考文献：
  名称：

  Nucleic Acid Related Compounds. 93. A Solution for the Historic Problem of Regioselective Sugar−Base Coupling To Produce 9-Glycosylguanines or 7-Glycosylguanines¹

  摘要：

  Per(trimethylsilyl)-2-N-acylguanine derivatives and tetra-O-acylpentofuranoses were coupled [tin-(IV) chloride or titanium(IV) chloride catalysis] to give predominant formation of 7-glycosylguanines. With TiCl4, a fortuitous organic/aqueous partitioning allowed isolation of 7-glycosylguanines from the 7/9 isomer mixtures. Per(trimethylsilyl)-2-N-acyl-6-O-(diphenylcarbamoyl)guanine derivatives and tetra-O-acylpentofuranoses underwent regioselective coupling (trimethylsilyl trifluoromethane-sulfonate catalysis) to give 9-glycosylguanines. The 6-O-(diphenylcarbamoyl)peracyl-9-beta-D-ribofuranosyl isomer was shown to be both the kinetic and thermodynamic coupling product. Deprotection of all of the peracyl coupling products was effected under mild conditions to give good to high yields of guanine nucleoside analogues. These methodologies provide solutions for the regioselective synthesis of 7- and 9-glycosylguanine nucleosides.

  DOI：

  10.1021/jo9617023

文献信息

• High-yield regioselective synthesis of 9-glycosyl guanine nucleosides and analogues via coupling with 2-<i>N</i>-acetyl-6-<i>O</i>-diphenylcarbamoylguanine
  作者：Ruiming Zou、Morris J. Robins

  DOI：10.1139/v87-243

  日期：1987.6.1

  Treatment of 2-N,9-diacetylguanine with diphenylcarbamoyl chloride followed by heating with aqueous ethanol gave 2-N-acetyl-6-O-diphenylcarbamoylguanine (2-acetamido-6-diphenylcarbamoyloxypurine). Bis-trimethylsilylation of this product followed by coupling with glycosyl acetates (trimethylsilyl triflate catalysis) or α-haloethers in anhydroustoluene gave 9-substituted guanine compounds in high yields

  用二苯基氨基甲酰氯处理 2-N,9-二乙酰鸟嘌呤，然后用乙醇水溶液加热，得到 2-N-乙酰基-6-O-二苯基氨基甲酰鸟嘌呤（2-乙酰氨基-6-二苯基氨基甲酰氧基嘌呤）。该产物的双三甲基甲硅烷基化，然后与乙酸糖酯（三氟甲磺酸三甲基甲硅烷酯催化）或无水甲苯中的 α-卤醚偶联，以高产率得到 9-取代的鸟嘌呤化合物，未检测到 7-异构体。
• The Determinative Influence of the O⁶-(Diphenylcarbamoyl) Group on the Exocyclic Nitrogen Benzylation in 2-Amino-6-oxopurine Derivatives
  作者：Marina Madre、Marina Petrova、Sergey Belyakov

  DOI：10.1055/s-2008-1067254

  日期：2008.10

  A series of novel 2-(benzylamino)-6-oxopurine derivatives has been synthesized by arylalkylation of the corresponding 2-(acetylamino)-6-(diphenylcarbamoyloxy)purines. The decisive role of the temporary O6-(diphenylcarbamoyl) protection on the benzylation of the exocyclic amino group in 2-(acetylamino)-6-oxopurines has been demonstrated.

  一系列新型的2-(苄基氨基)-6-氧嘌呤衍生物是通过相应的2-(乙酰氨基)-6-(二苯基氨基羧酰氧)嘌呤的芳基烷基化合成的。已证明临时的O6-(二苯基氨基酰)保护在2-(乙酰氨基)-6-氧嘌呤中对外环氨基的苄基化起着决定性作用。
• ZOU, RUIMING;ROBINS, MORRIS J., CAN. J. CHEM., 65,(1987) N 6, 1436-1437
  作者：ZOU, RUIMING、ROBINS, MORRIS J.

  DOI：——

  日期：——