N-(1-adamantyl)-4-amino-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyridmidine-5-carboxamide

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: N-(1-adamantyl)-4-amino-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyridmidine-5-carboxamide
• 英文别名: N^amido-(1-adamantyl)sangivamycin；N-(1-adamantyl)-4-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carboxamide
• 化学式: C₂₂H₂₉N₅O₅
• 分子量: 443.503
• InChiKey: WBQQWLVLNAFCQX-OZDXKGLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  156
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-金刚烷醇 、 4-氨基-5-氰基-7-(beta-d-呋喃核糖)吡咯并[2,3-d]嘧啶 在 三氟乙酸 作用下， 反应 1.0h， 以21%的产率得到N-(1-adamantyl)-4-amino-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyridmidine-5-carboxamide
  参考文献：
  名称：

  Studies on the Adamantylation ofN-Heterocycles and Nucleosides

  摘要：

  Adamantylation of several N-heterocycles and of two ribonucleosides (uridine and toyocamycin) was studied. The exact substitution position by the adamantyl carbocation generated tram adamantan-1-ol in CF3COOH depends on the nature of the heterocyclic substrate. Thus, adamantylation of an additional exocyclic amino group (see Scheme 1), N-adamantylation of the heterocycle (Scheme 2), C-adamantylation of the heterocycle (Scheme 3), as well as the formation of heterocyclic N-adamantylcarboxamides via the Ritter reaction (Scheme 4) are possible. The structures of the reaction products were determined by means of elemental analysis and NMR, UV,and IR spectroscopy.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<2020::aid-hlca2020>3.0.co;2-p

文献信息

• Studies on the Adamantylation ofN-Heterocycles and Nucleosides
  作者：Zygmunt Kazimierczuk、Andrzej Orzeszko

  DOI：10.1002/(sici)1522-2675(19991110)82:11<2020::aid-hlca2020>3.0.co;2-p

  日期：1999.11.10

  Adamantylation of several N-heterocycles and of two ribonucleosides (uridine and toyocamycin) was studied. The exact substitution position by the adamantyl carbocation generated tram adamantan-1-ol in CF3COOH depends on the nature of the heterocyclic substrate. Thus, adamantylation of an additional exocyclic amino group (see Scheme 1), N-adamantylation of the heterocycle (Scheme 2), C-adamantylation of the heterocycle (Scheme 3), as well as the formation of heterocyclic N-adamantylcarboxamides via the Ritter reaction (Scheme 4) are possible. The structures of the reaction products were determined by means of elemental analysis and NMR, UV,and IR spectroscopy.