2',3',5'-tri-O-benzoyladenosine | 51549-15-6

• 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',3',5'-tri-O-benzoyladenosine
• 英文别名: 9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-adenine；adenosine 2',3',5'-tri-O-benzoate；O^2'_,O3'_,O5'-tribenzoyl-adenosine；O^2'_,O3'_,O5'-Tribenzoyl-adenosin；[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
• CAS: 51549-15-6
• 化学式: C₃₁H₂₅N₅O₇
• 分子量: 579.569
• InChiKey: DEVINOMUNOYSFC-ZYWWQZICSA-N

物化性质

• 熔点：
  92-96 °C
• 沸点：
  787.6±70.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-benzoyladenosine 在 sodium tetrahydroborate 、 sodium methylate 、 羟胺乙酸盐 、 乙酸酐 作用下， 以 吡啶 为溶剂， 反应 26.0h， 生成 阿糖腺苷
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-脱氧腺苷 在 吡啶 、 咪唑 、 四氯化锡 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.17h， 生成 2',3',5'-tri-O-benzoyladenosine
  参考文献：
  名称：

  Effective Anomerisation of 2′‐Deoxyadenosine Derivatives During Disaccharide Nucleoside Synthesis

  摘要：

  The formation of a disaccharide nucleoside (11) by O3'-glycosylation of 5'-O-protected 2'-deoxyadenosine or its N-6-benzoylated derivative has been observed to be accompanied by anomerisation to the corresponding alpha-anomeric product (12). The latter reaction can be explained by instability of the N-glycosidic bond of purine 2'-deoxynucleosides in the presence of Lewis acids. An independent study on the anomerisation of partly blocked 2'-deoxyadenosine has been carried out. Additionally, transglycosylation has been utilized in the synthesis of 3'-O-beta-D-ribofuranosyl-2'deoxyadenosines and its alpha-anomer.

  DOI：

  10.1081/ncn-200040627

文献信息

• 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。
• Enhanced solubility and selective benzoylation of nucleosides in novel ionic liquid
  作者：Vineet Kumar、Virinder S. Parmar、Sanjay V. Malhotra

  DOI：10.1016/j.tetlet.2006.11.155

  日期：2007.1

  Solubility and benzoylation study of both ribo- and deoxyribonucleosides is reported in a new ionic liquid MoeMIM·TFA; high selectivity for O-benzoylation is achieved.

  新型离子液体MoeMIM·TFA报道了核糖核苷和脱氧核糖核苷的溶解度和苯甲酰化研究。实现了对O-苯甲酰化的高选择性。
• 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。
• ‘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。
• CuI Controlled C–C and C–N Bond Formation of Heteroaromatics through C(sp³)–H Activation
  作者：Ran Xia、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/ol302640e

  日期：2012.11.2

  A new method for C–C and C–N bond formation of heteroaromatics and C(sp3)–H alkanes was developed with high regioselectivity. The reaction occurred on C8 to give 8-cylcoakylpurines by C–C bond formation only promoted by tBuOOtBu, while it occurred on the amino group to give N6-alkylated purines by C–N bond formation when 2 equiv of CuI were added. A reaction mechanism was also proposed based on our

  具有高区域选择性的杂芳烃和C（sp 3）-H烷烃的C–C和C–N键形成的新方法得到了发展。该反应发生在C8上，仅通过t BuOO t Bu促进了通过C–C键形成的8烷基甲酰基嘌呤，而当氨基当上，当2当量的CuI为2时，通过C–N键的形成产生了N 6烷基化的嘌呤。添加。根据我们的初步实验数据，还提出了一种反应机理。