1-[(2R,3S,4R,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(4-methylphenyl)sulfanyloxan-2-yl]-5-methylpyrimidine-2,4-dione | 1033090-79-7

• 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: 1-[(2R,3S,4R,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(4-methylphenyl)sulfanyloxan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1033090-79-7
• 化学式: C₁₈H₂₂N₂O₆S
• 分子量: 394.448
• InChiKey: DDQBYZIIXIIYAV-DRXUAVOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-[(2R,3S,4R,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(4-methylphenyl)sulfanyloxan-2-yl]-5-methylpyrimidine-2,4-dione 、 苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  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
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 1-[(2R,3S,4R,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-(4-methylphenyl)sulfanyloxan-2-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