4-fluoro-O¹,O²-isopropylidene-β-D-4-deoxy-sorbopyranose | 41342-43-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-fluoro-O¹,O²-isopropylidene-β-D-4-deoxy-sorbopyranose
• CAS: 41342-43-2
• 化学式: C₉H₁₅FO₅
• 分子量: 222.214
• InChiKey: DIYYLGSHTYNAAY-AYHNYZOXSA-N

反应信息

• 作为反应物：
  描述：

  4-fluoro-O¹,O²-isopropylidene-β-D-4-deoxy-sorbopyranose 在 硫酸 作用下， 生成 4-fluoro-α-D-4-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