5-fluoro-α-L-5-deoxy-sorbopyranose | 55908-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 5-fluoro-α-L-5-deoxy-sorbopyranose
• 英文别名: (2R,3S,4S,5S)-5-fluoro-2-(hydroxymethyl)oxane-2,3,4-triol
• CAS: 55908-32-2
• 化学式: C₆H₁₁FO₅
• 分子量: 182.149
• InChiKey: PGPPETLPAXXHBQ-BGPJRJDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-fluoro-α-L-5-deoxy-sorbopyranose 在 Ni(Me₄en)2Cl₂ 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以20%的产率得到(2S,3S,4S)-4-Fluoro-2,3,5-trihydroxy-pentanoic acid methyl ester
  参考文献：
  名称：

  Nickel(II)-Catalysed Transformations of 5-Azido-5-deoxy-d-glucofuranose and of 5-Azido-5-deoxy-l-idofuranose

  摘要：

  Nickel(II) catalysed isomerisation reactions of C-5 modified derivatives of D-glucose as well as L-idose were investigated. 5-Azido-5-deoxy-D-glucofuranose was successfully isomerised into the corresponding D-manno epimer in good yields. Contrasting this result, in the case of the 5-modified L-idofuranose probed, no evidence for successful epimerisation at C-2 could be found. However, this sugar was quantitatively rearranged into the corresponding L-sorbopyranose. Upon extended reaction periods, the latter underwent degradation to give the coresponding 4-modified methyl L-xylonate.

  DOI：

  10.1080/07328309808002325
• 作为产物：
  描述：

  5-fluoro-O¹,O²-isopropylidene-α-L-5-deoxy-sorbopyranose 在 硫酸 作用下， 生成 5-fluoro-α-L-5-deoxy-sorbopyranose
  参考文献：
  名称：

  Deoxyfluoroketohexoses: 4-deoxy-4-fluoro-D-sorbose and -tagatose and 5-deoxy-5-fluoro-L-sorbose

  摘要：

  4-Deoxy-4-fluoro-alpha-D-sorbose (6) was prepared in crystalline form by the action of potassium hydrogen fluoride on 3,4-anhydro-1,2-O-isopropylidene-beta-D-psicopyranose (3) followed by deacetonation. Under identical conditions, 3,4-anhydro-1,2-O-isopropylidene-beta-D-tagatopyranose (7) underwent epoxide migration to give 4,5-anhydro-1,2-O-isopropylidene-beta-D-fructopyranose (12), which after deacetonation yielded 4-deoxy-4-fluoro-D-tagatose (15) and 5-deoxy-5-fluoro-alpha-L-sorbopyranose (16), the latter as the crystalline, free sugar. The action of glycol-cleavage reagents on the isopropylidene acetals of the deoxyfluoro sugars was consistent with the assigned structures. The structures were established by 13-C n.m.r. studies of the free deoxyfluoro sugars 6 and 16 and of the isopropylidene acetal 13, and by 1-H n.m.r. studies on the acetylated isopropylidene acetals 5 diacetate, 13 diacetate, and 14 diacetate. 5-Deoxy-5-fluoro-L-sorbose (16) was biologically active, producing in mice effects characteristic of deoxyfluorotrioses and of fluoroacetate. 4-Deoxy-4-fluoro-D-tagatose (15) and 4-deoxy-4-fluoro-D-sorbose (6) produced no apparent effects in mice up to a dose of 500mg/kg. The implications of these findings with respect to transport, phosphorylation, and the action of aldolase on ketohexoses are discussed.

  DOI：

  10.1016/s0008-6215(00)82612-9