1-[(2R,4aR,8aR)-8-(4-methylphenyl)sulfonyl-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl]-5-methylpyrimidine-2,4-dione | 1033090-81-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(2R,4aR,8aR)-8-(4-methylphenyl)sulfonyl-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1033090-81-1
• 化学式: C₂₅H₂₄N₂O₇S
• 分子量: 496.541
• InChiKey: XBLAVYUVMDEKTE-AYUHEPSNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(2R,4aR,6R,7S,8R,8aR)-6-(5-methyl-2,4-dioxopyrimidin-1-yl)-8-(4-methylphenyl)sulfonyl-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] methanesulfonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-[(2R,4aR,8aR)-8-(4-methylphenyl)sulfonyl-2-phenyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  Studies on the synthesis and unusual behavior of vinyl sulfone-modified hexenopyranosylthymines

  摘要：

  Although vinyl sulfone-modified- (VSM) pent-2-enofuranosyl nucleosides 2 and hex-2-enopyranosyl glycoside 4 are easily synthesized from the corresponding mesylated sulfones le and 3c, respectively, via an oxidation-mesylation-elimination route, the 3'-C-sulfonyl-hex-2'-enopyranosylthymine 11 is not obtained from 10 and a glycal derivative 12 is formed instead. On the other hand, 3-C-sulfonyl-hex-3'-enopyranosylthymine 20 is easily synthesized from the mesylated sulfone 19. Again unlike the reaction patterns of VSM-pent-T-enofuranosyl nucleosides 2 and hex-2-enopyranosyl glycosides 4 as Michael acceptors, the reactions of nucleophiles with 3'-C-sulfonyl-hex-3'-enopyranosylthymine 20 yielded a rearranged product 21 instead of Michael adducts. (c) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2008.02.016