2'-deoxyformycin B | 42821-83-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2'-deoxyformycin B
• 英文别名: 3-(β-D-erythro-2-deoxy-pentofuranosyl)-1(2),6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one；3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2,6-dihydropyrazolo[4,3-d]pyrimidin-7-one
• CAS: 42821-83-0
• 化学式: C₁₀H₁₂N₄O₄
• 分子量: 252.23
• InChiKey: AQJBRKFYNVRBQQ-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2'R)-cis-3-<2',5'-dihydro-4'-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-5'-(hydroxymethyl)-2'-furanyl>-1-(tetrahydropyran-2-yl)-7-<(tetrahydropyran-2-yl)oxy>pyrazolo<4,3-d>pyrimidine 在 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 甲醇 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 72.17h， 生成 2'-deoxyformycin B
  参考文献：
  名称：

  Syntheses of 2'-deoxypseudouridine, 2'-deoxyformycin B, and 2',3'-dideoxyformycin B by palladium-mediated glycal-aglycon coupling

  摘要：

  5-Iodouracil and the ribofuranoid glycal 1,4-anhydro-2-deoxy-3-O-[(1,1-dimethylethyl)diphenylsilyl]-D-erythro-pent-1-enitol underwent regio- and stereospecific coupling in the presence of catalytic palladium acetate and either triphenylphosphine or triphenylarsine ligands. The resulting C-glycosyl product was converted to 2'-deoxypseudouridine, 5-(2'-deoxy-beta-D-ribofuranosyl)-2,4(1H,3H)-pyrimidinedione (63% overall yield). In a similar way, 2'-deoxyformycin B, 3-(2'-deoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, and 2,3'-dideoxyformycin B, 3-(2',3'-dideoxy-beta-D-ribofuranosyl)pyrazolo[4,3-d]pyrimidin-7-one, have been synthesized by reaction sequences in which the key step is a palladium-mediated regio- and stereospecific C-glycosyl bond forming reaction between this furanoid glycal and a bis(tetrahydropyranyl)-protected 3-iodopyrazolo[4,3-d]pyrimidine aglycon derivative.

  DOI：

  10.1021/jo00043a029

文献信息

• Nucleic Acid Related Compounds. 5. The Transformation of Formycin and Tubercidin into 2′- and 3′-Deoxynucleosides
  作者：Morris J. Robins、James R. McCarthy Jr.、Roger A. Jones、Rudolf Mengel

  DOI：10.1139/v73-198

  日期：1973.5.1

  Reaction of tubercidin (4-amino-7-β-D-ribofuranosylpyrrolo[2,3-d]pyrimidine) (1) with α-acetoxyisobutyryl chloride in the presence of excess sodium iodide in acetonitrile gave an acylated iodo intermediate (2) which was converted into 3′-deoxytubercidin (4) by hydrogenolysis and subsequent saponification.Analogous treatment of formycin (7-amino-3-β-D-ribofuranosylpyrazolo[4,3-d]pyrimidine) (5) gave

  结核菌素（4-氨基-7-β-D-呋喃核糖基吡咯并[2,3-d]嘧啶）(1) 与 α-乙酰氧基异丁酰氯在乙腈中过量碘化钠存在下反应得到酰化碘中间体 (2)通过氢解和随后的皂化将其转化为 3'-脱氧结核菌素 (4)。类似处理福尔霉素 (7-amino-3-β-D-ribofuranosylpyrazolo[4,3-d]pyrimidine) (5) 得到 3'-deoxyformycin ( 6) 和 2'-脱氧甲霉素 (7) 的比例约为 3:2。这些纯化的核苷 6 和 7 分别通过酶促脱氨基得到 3'-脱氧甲霉素 B (8) 和 2'-脱氧甲霉素 B(9)。讨论了这些抗生素衍生的脱氧核苷的生物学原理、核磁共振和质谱。