| 1259317-85-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1259317-85-5
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: AYPWYMGHPBRROF-NWANDNLSSA-N

反应信息

• 作为反应物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以0.32 g的产率得到(2R,3R,6S)-N-benzyloxycarbonyl-6-methyl-2-hydroxymethylpiperidin-3-ol
  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
• 作为产物：
  描述：

  2,2,7-trimethyl-N-benzyloxycarbonyl-perhydro[1,3]dioxolo[4',5':4,5]furo[3,2-b]pyridine 在 三氟乙酸 、 sodium periodate 作用下， 以 水 、 丙酮 为溶剂， 反应 2.5h， 生成
  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