1,3-dimethyl-6-{(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidene-3-O-[(methylthio)thiocarbonyl]propyl}lumazine | 933803-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 1,3-dimethyl-6-{(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidene-3-O-[(methylthio)thiocarbonyl]propyl}lumazine
• 英文别名: O-[[(4S,5R)-5-(1,3-dimethyl-2,4-dioxopteridin-6-yl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl] methylsulfanylmethanethioate
• CAS: 933803-51-1
• 化学式: C₁₆H₂₀N₄O₅S₂
• 分子量: 412.491
• InChiKey: JPPFXCIWEHCQON-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-6-{(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidene-3-O-[(methylthio)thiocarbonyl]propyl}lumazine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以78%的产率得到1,3-dimethyl-6-[(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidenepropyl]lumazine
  参考文献：
  名称：

  Synthesis of 6- and 7-(1,2,3-Trihydroxy-1,2-O-isopropylidenepropyl)pteridines and Deoxygenation of Their 3’-Hydroxy Groups

  摘要：

  Treatment of 3,4-O-isopropylidene-L-threo-pentos-2-ulose (7) with 5,6-diamino-1,3-dimethyluracil (8) afforded 1,3-dimethyl-6-[(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidenepropyl]lumazine (9a) and its 7-substituted isomer (9b). Deoxygenation of 3'-hydroxy groups of 9a,b was investigated in connection with a practical transformation of neopterin into biopterin.

  DOI：

  10.3987/com-06-s(w)33
• 作为产物：
  描述：

  1,3-dimethyl-6-[(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidenepropyl]lumazine 、 二硫化碳 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以66%的产率得到1,3-dimethyl-6-{(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidene-3-O-[(methylthio)thiocarbonyl]propyl}lumazine
  参考文献：
  名称：

  Synthesis of 6- and 7-(1,2,3-Trihydroxy-1,2-O-isopropylidenepropyl)pteridines and Deoxygenation of Their 3’-Hydroxy Groups

  摘要：

  Treatment of 3,4-O-isopropylidene-L-threo-pentos-2-ulose (7) with 5,6-diamino-1,3-dimethyluracil (8) afforded 1,3-dimethyl-6-[(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidenepropyl]lumazine (9a) and its 7-substituted isomer (9b). Deoxygenation of 3'-hydroxy groups of 9a,b was investigated in connection with a practical transformation of neopterin into biopterin.

  DOI：

  10.3987/com-06-s(w)33

文献信息

• Synthesis of 6- and 7-(1,2,3-Trihydroxy-1,2-O-isopropylidenepropyl)pteridines and Deoxygenation of Their 3’-Hydroxy Groups
  作者：Tadashi Hanaya、Daisuke Takayama、Hiroshi Yamamoto

  DOI：10.3987/com-06-s(w)33

  日期：——

  Treatment of 3,4-O-isopropylidene-L-threo-pentos-2-ulose (7) with 5,6-diamino-1,3-dimethyluracil (8) afforded 1,3-dimethyl-6-[(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidenepropyl]lumazine (9a) and its 7-substituted isomer (9b). Deoxygenation of 3'-hydroxy groups of 9a,b was investigated in connection with a practical transformation of neopterin into biopterin.