N⁴-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine | 23624-64-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N⁴-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine
• 英文别名: N⁴,O^2',O^3',O^5'-tetrabenzoylcytidine；1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-N-benzoylcytosine；N1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-N4-benzoylcytosine；N⁴,2',3',5'-tetra-O-benzoylycytidine；N⁴,O^2'_,O3'_,O5'-tetrabenzoyl-cytidine；N⁴,O^2'_,O3'_,O5'-Tetrabenzoyl-cytidin；[(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 23624-64-8
• 化学式: C₃₇H₂₉N₃O₉
• 分子量: 659.652
• InChiKey: XCYORFRPTXBDDD-CSEBVFCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N⁴-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 胞苷
  参考文献：
  名称：

  High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries

  摘要：

  [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.

  DOI：

  10.1021/jo061885l
• 作为产物：
  描述：

  N4-苯甲酰基胞嘧啶 在 硫酸氢铵 、 三氟甲磺酸酐 、 4,4'-二甲苯亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 9.83h， 生成 N⁴-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine
  参考文献：
  名称：

  A general method for N-glycosylation of nucleobases promoted by (p-Tol)₂SO/Tf₂O with thioglycoside as donor

  摘要：

  35个核苷酸通过在高产率和β-立体选择性下，在（p-Tol）2SO/Tf2O的预活化下，将硫代糖苷与嘧啶和嘌呤偶联合成。

  DOI：

  10.1039/c5cc03617h

文献信息

• Regioselective protection of carbohydrate derivatives.
  作者：Shigeyoshi Nishino、Hatsuko Takamura、Yoshiharu Ishido

  DOI：10.1016/s0040-4020(01)87616-x

  日期：1986.1

  A simple treatment of fully aroylated purine and pyrimidine ribo-nucleosides with pulverized potassium tert-butoxide in tetrahydrofuran (THF) or dichloromethane under a controlled condition gave a mixture of the corresponding di-O-aroyl derivatives in which 2'-OH derivatives are preponderant over 3'-OH derivatives; 3',5'-di-O-benzoyluridine, N4, 3', 5'-tribenzoylcytidine, N4, 3', 5'-tri-o-toluoylcytidine

  在控制条件下，在四氢呋喃（THF）或二氯甲烷中，用粉碎的叔丁醇钾简单地处理完全芳基化的嘌呤和嘧啶核糖核苷，得到相应的二-O-芳酰基衍生物的混合物，其中2'-OH衍生物占优势超过3'-OH衍生物；3' ，5'-二-O- benzoyluridine，N 4，3' ，5'-tribenzoylcytidine，N 4，3' ，5'-三-邻- toluoylcytidine，N 2，3' ，5'-tribenzoylguanosine，和获得N 2-异丁酰基-3'，5'-二-O-苯甲酰基鸟苷结晶，产率分别为80％，78％，72％，67％和65％。
• A Reverse Strategy for synthesis of nucleosides based on n-pentenyl orthoester donors
  作者：Bert Fraser-Reid、Parimala Ganney、Changalvala V. S. Ramamurty、Ana M. Gómez、J. Cristóbal López

  DOI：10.1039/c3cc41036f

  日期：——

  Strategically derivatized NPOE glycosyl donors, are able to efficiently glycosylate silylated nucleobases under mild conditions, even as low as −78 °C if necessary. Ensuring trans-1,2 glycosylation, thus permitting, unlike classical procedures, a Reverse Strategy for the synthesis of ribonucleosides, where glycosylation occurs late, rather than early, and convergency is optimized.

  战略性衍生化的NPOE糖苷供体能够在温和条件下高效地糖苷化硅烷化的核苷碱碱基，必要时甚至可以低至−78°C。这确保了反式-1,2糖苷化，从而与传统方法不同，允许采用反向策略合成核糖核苷，在这种策略中，糖苷化发生得较晚，而不是较早，并且优化了收敛性。
• Benzoyl Cyanide: A Mild and Efficient Reagent for Benzoylation of Nucleosides
  作者：Ashok K. Prasad、Vineet Kumar、Jyotirmoy Maity、Zhiwei Wang、Vasulinga T. Ravikumar、Yogesh S. Sanghvi、Virinder S. Parmar

  DOI：10.1081/scc-200051693

  日期：2005.4.1

  Abstract Efficient benzoylation of various nucleosides has been accomplished in pyridine with a catalytic amount of DMAP and benzoyl cyanide under mild conditions.

  摘要 在温和条件下，使用催化量的 DMAP 和苯甲酰氰在吡啶中实现了各种核苷的有效苯甲酰化。
• Partial protection of carbohydrate derivatives. part 18. simple, preparative procedure for 5'--acylribonucleosides; highly regioselective -deacylation at 2' and 3' positions of fully acylated purine and pyrimidine ribonucleoside through sodium methoxide-thf system
  作者：Shigeyoshi Nishino、Md.Azizur Rahman、Hatsuko Takamura、Yoshiharu Ishido

  DOI：10.1016/s0040-4020(01)91350-x

  日期：1985.1

  A treatment of fully acylated purine and pyrimidine ribonucleosides with a small excess amount of sodium methoxide in THF at room temperature gave the corresponding 5'-acylates in excellent yields; N-acyl groups on the nucleic acid base moieties of adenosine and cytidine in addition to guanosine derivatives satisfactorily survived under the conditions used.

  在室温下用少量过量的甲醇钠在THF中处理完全酰化的嘌呤和嘧啶核糖核苷，得到的相应5'-酰化物收率很好；除鸟苷衍生物外，腺苷和胞苷的核酸碱基部分上的N-酰基在所使用的条件下令人满意地存活。
• ‘Green’ methodology for efficient and selective benzoylation of nucleosides using benzoyl cyanide in an ionic liquid
  作者：Ashok K. Prasad、Vineet Kumar、Shashwat Malhotra、Vasulinga T. Ravikumar、Yogesh S. Sanghvi、Virinder S. Parmar

  DOI：10.1016/j.bmc.2005.04.038

  日期：2005.7

  Benzoyl cyanide in the ionic liquid 1-methoxyethyl-3-methylimidazolium methanesulfonate has been employed as a 'green' alternative and mild reaction condition protocol to conventional pyridine-benzoyl chloride system for efficient and selective benzoylation of nucleosides (of both the ribo- and deoxyribo-series) at ambient temperatures. The use of benzoyl cyanide-ionic liquid combination has been successfully

  离子液体1-甲氧基乙基-3-甲基咪唑鎓甲磺酸盐中的苯甲酰氰已被用作常规吡啶-苯甲酰氯系统的“绿色”替代方案，反应条件温和，可用于核糖（核糖和脱氧核糖两者）的有效和选择性苯甲酰化系列）。苯甲酰基氰化物-离子液体组合的使用已成功扩展到酚，芳族胺，苄醇，脂肪族二醇，3-氨基苯酚和2-氨基苄基醇的高效苯甲酰化，这表明该苯甲酰化体系的多功能性。