N6-benzoyl-9-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-α-D-erythro-pentofuranosyl]adenine | 858672-57-8

• 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: N6-benzoyl-9-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-α-D-erythro-pentofuranosyl]adenine
• 英文别名: N⁶-benzoyl-9-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-α-D-erythro-pentofuranosyl]adenine
• CAS: 858672-57-8
• 化学式: C₅₉H₅₅N₅O₁₁Si
• 分子量: 1038.2
• InChiKey: TZIMZTUAQHGGQW-CCGUFCITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.36
• 重原子数：
  76.0
• 可旋转键数：
  17.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  188.52
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  N6-benzoyl-9-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-α-D-erythro-pentofuranosyl]adenine 在 四丁基氟化铵 、 氨 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.75h， 生成 9-(3-O-β-D-ribofuranosyl-2-deoxy-α-D-erythro-pentofuranosyl)adenine
  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
• 作为产物：
  描述：

  N-苯甲酰基-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 1.67h， 生成 N6-benzoyl-9-[5-O-tert-butyldiphenylsilyl-3-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-deoxy-α-D-erythro-pentofuranosyl]adenine
  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