(2R,3R)-3-azido-1,4-bis(benzyloxy)butan-2-ol | 876609-55-1

• 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-1,4-bis(benzyloxy)butan-2-ol
• 英文别名: (2R,3R)-3-azido-1,4-bis(phenylmethoxy)butan-2-ol
• CAS: 876609-55-1
• 化学式: C₁₈H₂₁N₃O₃
• 分子量: 327.383
• InChiKey: OZBQNHUWKBRCRY-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 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：
  0.33
• 拓扑面积：
  87.45
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-azido-1,4-bis(benzyloxy)butan-2-ol 在 4-二甲氨基吡啶 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 1-[(2S,3S)-2,3-bis(phenylmethoxymethyl)aziridin-1-yl]propan-1-one
  参考文献：
  名称：

  On the use of C2-symmetric aziridines as chiral auxiliaries

  摘要：

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

  DOI：

  10.1016/s0040-4020(01)85546-0
• 作为产物：
  描述：

  (S,S)-1,4-bis(benzyloxy)-2,3-epoxybutane 在 sodium azide 、 氯化铵 作用下， 以 丙醇 、 水 为溶剂， 反应 2.0h， 以94%的产率得到(2R,3R)-3-azido-1,4-bis(benzyloxy)butan-2-ol
  参考文献：
  名称：

  On the use of C2-symmetric aziridines as chiral auxiliaries

  摘要：

  A systematic study has been made of the utility of readily available C-2-symmetric aziridines as auxiliaries for asymmetric alkylation and aldol reactions of amide enolates. Aziridines with suitably placed oxygen atoms in the side chains proved to be useful for alkylation reactions (d.e. values up to >98%) and the results are explained in terms of an intramolecularly chelated Z-enolate species, which could be observed directly by means of NMR spectroscopy. In contrast, aziridine auxiliaries lacking side-chain oxygens performed better in aldol reactions (syn selectivity up to 98% d.e.) for which a Zimmerman-Traxler transition state is proposed. After reaction, the auxiliaries can be cleaved off nondestructively under mild conditions to afford either optically pure aldehydes or carboxylic acids.

  DOI：

  10.1016/s0040-4020(01)85546-0

文献信息

• Chemoenzymatic route to stereodefined 2-(azidophenyl)oxazolines for click chemistry
  作者：Paige J. Monsen、Frederick A. Luzzio

  DOI：10.1016/j.tetlet.2020.152717

  日期：2021.1

  the Staudinger/aza-Wittig to give the corresponding (4R,5R)-disubstituted-2-(4-nitrophenyl) oxazoline. Selective reduction of the nitrophenyloxazoline to the corresponding aminophenyloxazoline using aluminum amalgam followed by direct azidation of the 2-(4-aminophenyl) moiety provided the corresponding (4R,5R)-2-(4-azidophenyl) oxazoline derivative. The azidophenyl oxazoline was reacted with a proven

  将外消旋二保护 2-叠氮基-1-烷醇的芳基取代酯进行施陶丁格/氮杂-维蒂希反应，以评估其环化为相应的 2,4,5-三取代恶唑啉的范围并建立条件。在环化研究之后，通过将相应的外消旋叠氮乙酸酯与猪肝酯酶 (PLE) 温育，以高 ee 获得叠氮烷醇的 (2 R, 3 R )-对映体。对映体富集的 2-叠氮基-1-醇的对硝基苯甲酸酯通过 Staudinger/aza-Wittig 环化得到相应的 (4 R ,5 R)-二取代的-2-(4-硝基苯基)恶唑啉。使用铝汞齐将硝基苯基恶唑啉选择性还原为相应的氨基苯基恶唑啉，然后将 2-(4-氨基苯基) 部分直接叠氮化，提供相应的 (4 R ,5 R )-2-(4-叠氮基苯基) 恶唑啉衍生物。在铜/抗坏血酸钠的介导下，叠氮苯基恶唑啉与经过验证的点击伙伴 4-乙炔基氟苯反应，以高产率提供点击三唑产物。
• Tanner David, Birgersson Carin, Gogoll Adolf, Luthman Kristina, Tetrahedron, 50 (1994) N 32, S 9797-9824
  作者：Tanner David, Birgersson Carin, Gogoll Adolf, Luthman Kristina

  DOI：——

  日期：——