(5Z)-3-azido-1,2-O-isopropylidene-3,5,6,8-tetradeoxy-α-D-xylo-oct-5-ene-furanos-7-ulose | 1259317-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5Z)-3-azido-1,2-O-isopropylidene-3,5,6,8-tetradeoxy-α-D-xylo-oct-5-ene-furanos-7-ulose
• CAS: 1259317-79-7
• 化学式: C₁₁H₁₅N₃O₄
• 分子量: 253.258
• InChiKey: LHUNIBJKLDAYSH-HNIJHUQKSA-N

反应信息

• 作为产物：
  描述：

  1-三苯基膦-2-丙酮 、 3-azido-3-deoxy-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (5E)-3-azido-1,2-O-isopropylidene-3,5,6,8-tetradeoxy-α-D-xylo-oct-5-ene-furanos-7-ulose 、 (5Z)-3-azido-1,2-O-isopropylidene-3,5,6,8-tetradeoxy-α-D-xylo-oct-5-ene-furanos-7-ulose
  参考文献：
  名称：

  Intramolecular reductive cyclization strategy to the synthesis of (−)-6-methyl-3-hydroxy-piperidine-2-carboxylic acid, (+)-6-methyl-(2-hydroxymethyl)-piperidine-3-ol and their glycosidase inhibitory activity

  摘要：

  The first stereoselective synthesis of (2S, 3R, 6S)-6-methyl-3-hydroxy-piperidine-2-carboxylic acid (-)-6 and (2R, 3R, 6S)-6-methyl-(2-hydroxymethyl)-piperidine-3-ol (+)-7 was achieved starting from readily available D-glucose in 14 steps with 17% overall yield for both the compounds. The key feature of the present strategy includes the Wittig-olefination for the preparation of required conjugated keto-azide 9 and construction of 2,3,6-trisubstituted piperidine skeleton 11 by applying intramolecular reductive cyclization of conjugated keto-azide intermediate. The glycosidase inhibitory activity of compounds 6 and 7 towards several glycosidases has been evaluated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.055