2-脱氧四氢尿苷 | 31962-88-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-脱氧四氢尿苷
• 中文别名: 2'-脱氧-3,4,5,6-四氢尿苷
• 英文名称: 2'-deoxytetrahydrouridine
• 英文别名: dTHU；tetrahydro-2'-deoxyuridine；4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-diazinan-2-one
• CAS: 31962-88-6
• 化学式: C₉H₁₆N₂O₅
• 分子量: 232.236
• InChiKey: RSRNLJYSWSSQMW-CZLDRYSHSA-N

物化性质

• 沸点：
  617.8±55.0 °C(Predicted)
• 密度：
  1.488±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  102
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-脱氧四氢尿苷 在 氨 作用下， 反应 18.0h， 生成 4-methoxy-2'-deoxytetrahydrouridine
  参考文献：
  名称：

  Synthesis of Deoxytetrahydrouridine

  摘要：

  The alpha-hydroxyamido functionality of 2'-deoxytetrahydrouridine (dTHU) makes this seemingly simple and generally useful compound difficult to obtain. Reported synthetic strategies produce extremely poor yields and multiple products, and full characterization data is not available. Described herein is a two-step approach for synthesizing dTHU in increased yields and purity; stability concerns are also addressed. Catalytic reduction (5% Rh/alumina) of 2'-deoxyuridine. followed by reduction with sodium borohydride as a limiting reagent, produces dTHU and limits formation of side products. Evidence was obtained for formation of a methoxy-substituted analogue during purification. By this strategy, dTHU of >95% purity can be obtained in 40% yield on a 150 mg scale.

  DOI：

  10.1021/jo802599v
• 作为产物：
  描述：

  5,6-二氢脱氧尿苷 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 2.0h， 以41%的产率得到2-脱氧四氢尿苷
  参考文献：
  名称：

  Synthesis of Deoxytetrahydrouridine

  摘要：

  The alpha-hydroxyamido functionality of 2'-deoxytetrahydrouridine (dTHU) makes this seemingly simple and generally useful compound difficult to obtain. Reported synthetic strategies produce extremely poor yields and multiple products, and full characterization data is not available. Described herein is a two-step approach for synthesizing dTHU in increased yields and purity; stability concerns are also addressed. Catalytic reduction (5% Rh/alumina) of 2'-deoxyuridine. followed by reduction with sodium borohydride as a limiting reagent, produces dTHU and limits formation of side products. Evidence was obtained for formation of a methoxy-substituted analogue during purification. By this strategy, dTHU of >95% purity can be obtained in 40% yield on a 150 mg scale.

  DOI：

  10.1021/jo802599v

文献信息

• 2'-FLUORO-2'-DEOXYTETRAHYDROURIDINES AS CYTIDINE DEAMINASE INHIBITORS
  申请人：Eisai Inc.

  公开号：EP2207786B1

  公开（公告）日：2012-03-07