1-(2,3-anhydro-5-O-mesyl-β-D-lyxofuranosyl)uracil | 37445-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(2,3-anhydro-5-O-mesyl-β-D-lyxofuranosyl)uracil
• 英文别名: 1-(2,3-anhydro-5-O-mesyl-β-D-lyxofuranosyl)uraicil；1-(5-O-methylsulfonyl-2,3-epoxy-β-D-lyxofuranosyl)uracil；1-<2',3'-Epoxy-5'-O-methynsulfonyl-β-D-lyxosyl>-uracil；1-<5-O-Mesyl-2,3-epoxy-β-D-lyxofuranosyl>-uracil；1-(O⁵-methanesulfonyl-β-D-2,3-anhydro-lyxofuranosyl)-1H-pyrimidine-2,4-dione；[(1S,2R,4R,5S)-4-(2,4-dioxopyrimidin-1-yl)-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methyl methanesulfonate
• CAS: 37445-45-7
• 化学式: C₁₀H₁₂N₂O₇S
• 分子量: 304.28
• InChiKey: XCFALMNXUGOUDD-RSWFSCQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三甲基铝 、 1-(2,3-anhydro-5-O-mesyl-β-D-lyxofuranosyl)uracil 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 以39%的产率得到1-(2,5-anhydro-3-deoxy-3-methyl-β-D-arabinofuranosyl)uracil
  参考文献：
  名称：

  Reactivity of 2',3'-Anhydro Pyrimidine Nucleosides toward Trimethylaluminum

  摘要：

  Treatment of 2',3'-anhydro pyrimidine nucleoside derivatives (1) with trimethylaluminum afforded 1-(3-deoxy-3-methyl-beta-D-arabinofuranosyl)pyrimidine derivatives (2) and 1-(2-deoxy-2-methyl-beta-D-xylofuranosyl)pyrimidine derivatives (3) as a mixture in approximately 2 : 1 - 3 : 1 ratio via ring-opening of the epoxide involving the nucleophilic attack of trimethylaluminum at the 3' or 2'-position of 1.

  DOI：

  10.3987/com-99-s144

文献信息

• Azido-(amino-)furanosyl nucleosides and their phosphoramidates
  作者：Darinka Katalenić、Vinko Škarić

  DOI：10.1039/p19920001065

  日期：——

  The ring-opening of 2,2'-anhydro-1-[5-azido- 5 and 5-benzamido- 3 5-deoxy-3-O-methylsulfonyl-beta-D-arabinofuranosyl] uracil by the ion exchanger Dowex 50 (H+) afforded the corresponding 1-[5-azido-8 and 5-benzamido- 12 5-deoxy-3-O-methylsulfonyl-beta-D-arabinofuranosyl]uracil. Hydrogenolysis of the azido nucleosides over Pd-black in the presence of benzoic acid anhydride led to the corresponding benzamido nucleosides in high yields. The 5'-azido-2',3'-oxirane 10 on reaction with ethanolic ammonia generated 1-(3-amino-5-azido-3,5-dideoxy-beta-D-arabinofuranosyl)uracil 15 and 1-(2-amino-5-azido-2,5-dideoxy-beta-D-xylofuranosyl)uracil 16 in a ratio 2:1. The 5'-O-mesyl-2',3'-oxirane 25, on being treated with NaN3 in DMF at 100-degrees-C, afforded 2',5'-anhydro-1-(3-azido-3-deoxy-beta-D-arabinofuranosyl) uracil 26 (54.5%), 3',5'-diazido-beta-D-arabinofuranosyl 27 (20.6%) and 2',5'-diazido-beta-D-xylofuranosyl 28 (5.4%). The hydrogenolysis of 5 over Pd-black proceeded into 2,5'-imino-1-(3-O-methylsulfonyl-beta-D-arabinofuranosyl)uracil 32 which, as the 5'-benzamido derivative 36, was transformed into 3. The 5'-azido compound 5 and 10 on reaction with triphenyl phosphite in aqueous dioxane gave the respective 5'-diphenylphosphoramidate 38 and 39. Similarly, the 3'-azido compound 22 was converted into 3'-diphenylphosphoramidate 40.
• Formation of 4’,5’-Didehydro-5’-deoxy-3’-O-methyluridine via Regioselective Nucleophilic Addition of Methoxide Anion to 2’,3’-Anhydro-5’-dehydro-5’-iodouridine
  作者：Hironao Sajiki、Hideki Takasu、Kosaku Hirota

  DOI：10.3987/com-05-s(t)14

  日期：——

  Treatment of 2',3'-anhydro-5'-deoxy-5'-iodouracil (1) with sodium methoxide regioselectively provided 4',5'-didehydro-5'-deoxy-3'-O-methyl-uridine (2) as the sole product via 4',5'-didehydro-5'-deoxy-2',3'-epoxyuridine (6) as an intermediate.