2,3-anhydro-N,N-dibenzyl-4,6-O-ethylidene-D-altro-hexonamide | 1030597-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2,3-anhydro-N,N-dibenzyl-4,6-O-ethylidene-D-altro-hexonamide
• 英文别名: (2S,3R)-N,N-dibenzyl-3-[(2R,4R,5R)-5-hydroxy-2-methyl-1,3-dioxan-4-yl]oxirane-2-carboxamide
• CAS: 1030597-66-0
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: BMZXVVBRTWEBMA-WEUUYRGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,4R,5R)-5-羟基-2-甲基-1,3-二恶烷-4-甲醛 、 (N,N-dibenzylcarbamoylmethylene)dimethyl sulfurane 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2,3-anhydro-N,N-dibenzyl-4,6-O-ethylidene-D-altro-hexonamide 、 2,3-anhydro-N,N-dibenzyl-4,6-O-ethylidene-D-gluco-hexonamide
  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.