(5RS,6RS)-5-bromo-6-hydroxy-5,6-dihydrothymidine | 41380-48-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: (5RS,6RS)-5-bromo-6-hydroxy-5,6-dihydrothymidine
• 英文别名: 5-bromo-6-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,3-diazinane-2,4-dione
• CAS: 41380-48-7
• 化学式: C₁₀H₁₅BrN₂O₆
• 分子量: 339.143
• InChiKey: QXTLVJPXEUPBNF-SKAWGCAZSA-N

物化性质

• 密度：
  1.830±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5RS,6RS)-5-bromo-6-hydroxy-5,6-dihydrothymidine 生成 2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl-7-oxa-2,4-diazabicyclo[4.1.0]heptane-3,5-dione
  参考文献：
  名称：

  HARAYAMA, TAKASHI;YANADA, REIKO;IIO, KUMIKO;YONEDA, FUMIO, 14TH SYMP. NUCL. ACIDS CHEM., TOKUSHIMA, OCT. 30TH - NOV. 1ST, 1986, OXFO+

  摘要：

  DOI：
• 作为产物：
  描述：

  beta-胸苷 在 sodium hydroxide 、 水 、 溴 作用下， 以 phosphate buffer 为溶剂， 生成 (5RS,6RS)-5-bromo-6-hydroxy-5,6-dihydrothymidine
  参考文献：
  名称：

  Formation of a Methide Derivative upon Photolysis of Thymidine Bromohydrins

  摘要：

  Reaction of bromine with thymidine in aqueous solution produces, in high yield, the corresponding 5-bromo-6-hydroxy-5,6-dihydroderivative (thymidine bromohydrins). UVC photolysis of thymidine bromohydrins gives rise to a reactive intermediate that is converted into 5-(hydroxymethyl)-2'-deoxyuridine upon incubation in water. When the former compound is left in methanol, ethanol, or propanol, the corresponding 5-alkoxymethyl derivatives are produced. The proposed structure for the primary photolysis product of thymidine bromohydrins is a methide derivative of the thymine ring. This compound could be an interesting intermediate in the synthesis of methyl-substituted thymidine.

  DOI：

  10.1021/jo026606i