1,5-dideoxy-1,5-imino-2,4-di-O-benzyl-N,N-diethyl-D-mannopyranosiduronamide | 1030597-89-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,5-dideoxy-1,5-imino-2,4-di-O-benzyl-N,N-diethyl-D-mannopyranosiduronamide
• 英文别名: (2S,3R,4R,5R)-N,N-diethyl-4-hydroxy-3,5-bis(phenylmethoxy)piperidine-2-carboxamide
• CAS: 1030597-89-7
• 化学式: C₂₄H₃₂N₂O₄
• 分子量: 412.529
• InChiKey: FRGUFMMZZKEPSH-KAOXLYBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,5-dideoxy-1,5-imino-2,4-di-O-benzyl-N,N-diethyl-D-mannopyranosiduronamide 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以69%的产率得到2,4-di-O-benzyl-1-deoxymannojirimicin
  参考文献：
  名称：

  Synthesis of intermediates in the formation of hydroxy piperidines and 2-azido lactones from d-erythrose

  摘要：

  A new stereodivergent synthesis towards piperidine iminosugar and azido lactones is described. The reaction of ethylidene-D-erythrose with amide sulfur ylides gave two isomeric trans-epoxyamides which were converted to 2-azido derivatives. Hydrolysis of the allo isomer gave 2-azido-1,4-lactone while the manno isomer gave the open chain epoxyamide. The latter gave a DMJ derivative in two steps. Direct hydrolysis of ethylidene epoxyamides gave the 3,6-anhydro glyconamides. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.003
• 作为产物：
  描述：

  [(2R,3S,4R,5S)-5-azido-6-(diethylamino)-3-hydroxy-6-oxo-2,4-bis(phenylmethoxy)hexyl] 4-methylbenzenesulfonate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到1,5-dideoxy-1,5-imino-2,4-di-O-benzyl-N,N-diethyl-D-mannopyranosiduronamide
  参考文献：
  名称：

  Synthesis of intermediates in the formation of hydroxy piperidines and 2-azido lactones from d-erythrose

  摘要：

  A new stereodivergent synthesis towards piperidine iminosugar and azido lactones is described. The reaction of ethylidene-D-erythrose with amide sulfur ylides gave two isomeric trans-epoxyamides which were converted to 2-azido derivatives. Hydrolysis of the allo isomer gave 2-azido-1,4-lactone while the manno isomer gave the open chain epoxyamide. The latter gave a DMJ derivative in two steps. Direct hydrolysis of ethylidene epoxyamides gave the 3,6-anhydro glyconamides. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.02.003

文献信息

• Synthesis of intermediates in the formation of hydroxy piperidines and 2-azido lactones from d-erythrose
  作者：M. Soledad Pino-González、Noé Oña

  DOI：10.1016/j.tetasy.2008.02.003

  日期：2008.4

  A new stereodivergent synthesis towards piperidine iminosugar and azido lactones is described. The reaction of ethylidene-D-erythrose with amide sulfur ylides gave two isomeric trans-epoxyamides which were converted to 2-azido derivatives. Hydrolysis of the allo isomer gave 2-azido-1,4-lactone while the manno isomer gave the open chain epoxyamide. The latter gave a DMJ derivative in two steps. Direct hydrolysis of ethylidene epoxyamides gave the 3,6-anhydro glyconamides. (c) 2008 Elsevier Ltd. All rights reserved.