6-deoxy-L-xylo-3-hexulose | 148979-69-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-deoxy-L-xylo-3-hexulose
• 英文别名: (2R,4R,5S)-1,2,4,5-tetrahydroxyhexan-3-one
• CAS: 148979-69-5
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: IWASYLACXSGJPG-VPENINKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-deoxy-L-xylo-3-hexulose 在 氨 、 碘 、 三乙胺 、 hydroxylamine-O-sulfonic acid 作用下， 生成 3-azi-3,6-dideoxy-L-xylo-hexitol
  参考文献：
  名称：

  Photolysis of 2-azi-2-deoxy-d-arabino-hexitol and analogous hexitols; the ineffectiveness of certain carbohydrate diazirines as photoaffinity labels

  摘要：

  Three diazirines 2-azi-2-deoxy-D-arabino-hexitol (4), its 1-deoxy analogue (5), and 3-azi-3,6-dideoxy-L-xylo-hexitol (9) were synthesised and their products of photolysis analysed by TLC. Diazirine 4 gave exclusively 2-deoxy-D-arabino-hexose (12), 5 gave predominantly 1,2-dideoxy-D-erythro-3-hexulose (10) and 1-deoxy-D-glucitol (11), and 9 did not yield any main product. Carrying out the irradiation of 4 in D2O gave selectively (2S)-2-deoxy-D-arabino-(2-H-2)hexose (12a). The results indicate that photolysis of a diazirine flanked by a hydroxymethyl group, as in compound 4, leads to a rapid and stereoselective intramolecular reaction of the intermediate. This may be an explanation of why compound 4 is ineffective as a photoaffinity reagent for mannitol permease (D-mannitol-specific enzyme II) of the E. coli phosphotransferase system for which it is a substrate. A secondary hydroxymethylene group has a less pronounced effect and still allows some reaction with the medium.

  DOI：

  10.1016/0008-6215(93)84209-o
• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal 在 磷酸 、 4 A molecular sieve 、 镍 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 64.0h， 生成 6-deoxy-L-xylo-3-hexulose
  参考文献：
  名称：

  Photolysis of 2-azi-2-deoxy-d-arabino-hexitol and analogous hexitols; the ineffectiveness of certain carbohydrate diazirines as photoaffinity labels

  摘要：

  Three diazirines 2-azi-2-deoxy-D-arabino-hexitol (4), its 1-deoxy analogue (5), and 3-azi-3,6-dideoxy-L-xylo-hexitol (9) were synthesised and their products of photolysis analysed by TLC. Diazirine 4 gave exclusively 2-deoxy-D-arabino-hexose (12), 5 gave predominantly 1,2-dideoxy-D-erythro-3-hexulose (10) and 1-deoxy-D-glucitol (11), and 9 did not yield any main product. Carrying out the irradiation of 4 in D2O gave selectively (2S)-2-deoxy-D-arabino-(2-H-2)hexose (12a). The results indicate that photolysis of a diazirine flanked by a hydroxymethyl group, as in compound 4, leads to a rapid and stereoselective intramolecular reaction of the intermediate. This may be an explanation of why compound 4 is ineffective as a photoaffinity reagent for mannitol permease (D-mannitol-specific enzyme II) of the E. coli phosphotransferase system for which it is a substrate. A secondary hydroxymethylene group has a less pronounced effect and still allows some reaction with the medium.

  DOI：

  10.1016/0008-6215(93)84209-o