摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carbonitrile | 76265-54-8

中文名称
——
中文别名
——
英文名称
9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carbonitrile
英文别名
——
9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carbonitrile化学式
CAS
76265-54-8
化学式
C15H15N5O5
mdl
——
分子量
345.315
InChiKey
QBRAREWREPGATO-YNEHKIRRSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    0.48
  • 重原子数:
    25.0
  • 可旋转键数:
    4.0
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.47
  • 拓扑面积:
    129.22
  • 氢给体数:
    0.0
  • 氢受体数:
    10.0

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量
  • 下游产品
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carbonitrileammonium hydroxide双氧水 作用下, 以 甲醇 为溶剂, 反应 21.0h, 以46%的产率得到9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carboxamide
    参考文献:
    名称:
    Synthesis and biological evaluation of certain 2'-deoxy-.beta.-D-ribo-and 2.beta.-D-arabinofuranosyl nucleosides of purine-6-carboxamide and 4,8-diaminopyrimido[5,4-d]pyrimidine
    摘要:
    The key intermediate 9-(2,3,5,-tri-O-acetyl-beta-D-arabinofuranosyl)purine-6-carbonitrile (7) was synthesized in four steps from 9-beta-D-arabinofuranosylpurine-6-thione (3) via 6-(methylsulfonyl)-9-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)purine (6). Reaction of compound 7 with methanolic ammonia provided the rearranged compound 4-amino-8-(beta-D-arabinofuranosylamino)pyrimido[5,4-d]pyrimidine (8). Treatment of 7 with ammonium hydroxide and hydrogen peroxide provided 9-beta-D-arabinofuranosylpurine-6-carboxamide (9). Compound 7 was also treated with sodium hydrosulfide to yield 9-beta-D-arabinofuranosylpurine-6-thiocarboxamide (10). Similarly, 9-(2-deoxy-3,5-di-O-acetyl-beta-D-erythro-pentofuranosyl)purine 6-carbonitrile (17) was prepared from 6-chloro-9-(2-deoxy-beta-D-erythro-pentofluranosyl)purine (11) via 9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine-6-thione. Compound 17 was converted into 4-amino-8-[(2-deoxy-beta-D-erythro-pentofuranosyl)amino]pyrimido[5,4-d]pyrimidi ne (18) and 9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine-6-carboxamide (20), respectively. Compound 2 showed immunosuppressive activity and also inhibited the growth of L-1210 leukemia in mice. Arabinonucleoside analogues 8-10 were inactive when tested against RNA and DNA viruses in cell culture.
    DOI:
    10.1021/jm00136a008
  • 作为产物:
    描述:
    ((2R,3S,5R)-3-乙酰氧基-5-(6-(甲硫基)-9H-嘌呤-9-基)四氢呋喃-2-基)乙酸甲酯 在 间氯过氧苯甲酸 作用下, 以 乙醚N,N-二甲基甲酰胺 为溶剂, 反应 7.5h, 生成 9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carbonitrile
    参考文献:
    名称:
    Synthesis and biological evaluation of certain 2'-deoxy-.beta.-D-ribo-and 2.beta.-D-arabinofuranosyl nucleosides of purine-6-carboxamide and 4,8-diaminopyrimido[5,4-d]pyrimidine
    摘要:
    The key intermediate 9-(2,3,5,-tri-O-acetyl-beta-D-arabinofuranosyl)purine-6-carbonitrile (7) was synthesized in four steps from 9-beta-D-arabinofuranosylpurine-6-thione (3) via 6-(methylsulfonyl)-9-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)purine (6). Reaction of compound 7 with methanolic ammonia provided the rearranged compound 4-amino-8-(beta-D-arabinofuranosylamino)pyrimido[5,4-d]pyrimidine (8). Treatment of 7 with ammonium hydroxide and hydrogen peroxide provided 9-beta-D-arabinofuranosylpurine-6-carboxamide (9). Compound 7 was also treated with sodium hydrosulfide to yield 9-beta-D-arabinofuranosylpurine-6-thiocarboxamide (10). Similarly, 9-(2-deoxy-3,5-di-O-acetyl-beta-D-erythro-pentofuranosyl)purine 6-carbonitrile (17) was prepared from 6-chloro-9-(2-deoxy-beta-D-erythro-pentofluranosyl)purine (11) via 9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine-6-thione. Compound 17 was converted into 4-amino-8-[(2-deoxy-beta-D-erythro-pentofuranosyl)amino]pyrimido[5,4-d]pyrimidi ne (18) and 9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine-6-carboxamide (20), respectively. Compound 2 showed immunosuppressive activity and also inhibited the growth of L-1210 leukemia in mice. Arabinonucleoside analogues 8-10 were inactive when tested against RNA and DNA viruses in cell culture.
    DOI:
    10.1021/jm00136a008
点击查看最新优质反应信息