(2R,3R)-3-azido-2,4-bis(benzyloxy)butanal | 1427467-84-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-3-azido-2,4-bis(benzyloxy)butanal
• CAS: 1427467-84-2
• 化学式: C₁₈H₁₉N₃O₃
• 分子量: 325.367
• InChiKey: WIUMCBQVEJWHSQ-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  24.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  84.29
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-azido-2,4-bis(benzyloxy)butanal 在 4-二甲氨基吡啶 、 potassium osmate(VI) dihydrate 、 正丁基锂 、 甲基磺酰胺 、 水 、 二正丁基氧化锡 、 potassium carbonate 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 11.0h， 生成
  参考文献：
  名称：

  A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-d-arabinitol using Co(III)(salen)-catalyzed hydrolytic kinetic resolution of a two-stereocentered anti-azido epoxide

  摘要：

  A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol, (+)-DAB-1, has been described in good overall yield (18.1%) and with high enantiomeric purity (up to 98% ee) starting from a simple raw material, cis-2-butene-1,4-diol. The Co-catalyzed hydrolytic kinetic resolution of a two-stereocentered racemic azido epoxide followed by asymmetric dihydroxylation of the alkene and 'one pot' reductive cyclisation of the azido diol are key reactions in the synthetic sequence. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.10.013
• 作为产物：
  描述：

  在 混旋樟脑磺酸 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2R,3R)-3-azido-2,4-bis(benzyloxy)butanal
  参考文献：
  名称：

  A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-d-arabinitol using Co(III)(salen)-catalyzed hydrolytic kinetic resolution of a two-stereocentered anti-azido epoxide

  摘要：

  A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol, (+)-DAB-1, has been described in good overall yield (18.1%) and with high enantiomeric purity (up to 98% ee) starting from a simple raw material, cis-2-butene-1,4-diol. The Co-catalyzed hydrolytic kinetic resolution of a two-stereocentered racemic azido epoxide followed by asymmetric dihydroxylation of the alkene and 'one pot' reductive cyclisation of the azido diol are key reactions in the synthetic sequence. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.10.013

文献信息

• Stereoselective synthesis of 1-deoxynojirimycin, D-glucono-δ-lactam and D-altrono-δ-lactam from a common chiral intermediate derived from D-mannitol
  作者：Mettu Ravinder、Thatikonda Narendar Reddy、Budde Mahendar、Vaidya Jayathirtha Rao

  DOI：10.3998/ark.5550190.0013.925

  日期：——

  A stereoselective synthesis of 1-deoxynojirimycin, D-glucono-δ-lactam and D-altrono-δ-lactam were accomplished from a common chiral intermediate derived from D-mannitol. The key transformations in the synthesis include Miyashita C-2 selective endo-mode azide opening of epoxy alcohol and Sharpless asymmetric dihydroxylation.

  1-脱氧野尻霉素、D-葡萄糖酸-δ-内酰胺和 D-altrono-δ-内酰胺的立体选择性合成是从衍生自 D-甘露醇的常见手性中间体完成的。合成中的关键转化包括环氧醇的 Miyashita C-2 选择性内模式叠氮化物开环和 Sharpless 不对称二羟基化。