syn-2-azido-1,3,4-trihydroxy-butane

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: syn-2-azido-1,3,4-trihydroxy-butane
• 英文别名: (2R,3S)-3-azidobutane-1,2,4-triol
• 化学式: C₄H₉N₃O₃
• 分子量: 147.134
• InChiKey: WTDMEGHZIYGENC-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  75
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 syn-2-azido-1,3,4-trihydroxy-butane 在 porcine pancreatic lipase 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以94%的产率得到syn-2-azido-1,4-diacetoxy-3-hydroxybutane
  参考文献：
  名称：

  Enzymatic resolution of syn-2-azido-1,3,4-trihydroxybutane catalysed by lipases in the transesterification mode

  摘要：

  The enzymatic resolution of both syn-2-azido-1,3,4-trihydroxybutane 1 and syn-2-azido-1,4-diacetoxy-3-hydroxybutane 2 have been undertaken with different lipases as catalysts and vinyl acetate as acylating agent. Lipases Amano PS and Amano AK proved to be the superior catalysts for this resolution. Indeed, both enantiomers of 1 are easily available in good yields and very good e.e.s (up to >99%). The use of chiral HPLC with a Chiralcel OD-H column allowed the determination of e.e.s of both diacetate 2 and triacetate 3 (syn-2-azido-1,3,4-triacetoxybutane) in a single analysis and thus facilitated the precise control of the reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00045-8
• 作为产物：
  描述：

  (3-hydroxymethyl-oxiranyl)-methanol 在 sodium azide 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以91%的产率得到syn-2-azido-1,3,4-trihydroxy-butane
  参考文献：
  名称：

  Enzymatic resolution of syn-2-azido-1,3,4-trihydroxybutane catalysed by lipases in the transesterification mode

  摘要：

  The enzymatic resolution of both syn-2-azido-1,3,4-trihydroxybutane 1 and syn-2-azido-1,4-diacetoxy-3-hydroxybutane 2 have been undertaken with different lipases as catalysts and vinyl acetate as acylating agent. Lipases Amano PS and Amano AK proved to be the superior catalysts for this resolution. Indeed, both enantiomers of 1 are easily available in good yields and very good e.e.s (up to >99%). The use of chiral HPLC with a Chiralcel OD-H column allowed the determination of e.e.s of both diacetate 2 and triacetate 3 (syn-2-azido-1,3,4-triacetoxybutane) in a single analysis and thus facilitated the precise control of the reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00045-8

文献信息

• Preparation of enantioenriched tetraols and triolamines from a common epoxide
  作者：Makan Kaviani-Joupari、Michael P. Schramm

  DOI：10.1016/j.tetlet.2013.07.001

  日期：2013.9

  We identify a silylcyclopentene oxide that is amenable to several distinct asymmetric catalytic transformations providing access to enantio-enriched tetraol and triol-amines. The sequence employed allows for selective protection of one amine or alcohol from the four heteroatoms that are introduced into the carbon scaffold. (C) 2013 Elsevier Ltd. All rights reserved.
• Enzymatic resolution of syn-2-azido-1,3,4-trihydroxybutane catalysed by lipases in the transesterification mode
  作者：G Iacazio、D Martini、S Sanchez、B Faure

  DOI：10.1016/s0957-4166(00)00045-8

  日期：2000.4

  The enzymatic resolution of both syn-2-azido-1,3,4-trihydroxybutane 1 and syn-2-azido-1,4-diacetoxy-3-hydroxybutane 2 have been undertaken with different lipases as catalysts and vinyl acetate as acylating agent. Lipases Amano PS and Amano AK proved to be the superior catalysts for this resolution. Indeed, both enantiomers of 1 are easily available in good yields and very good e.e.s (up to >99%). The use of chiral HPLC with a Chiralcel OD-H column allowed the determination of e.e.s of both diacetate 2 and triacetate 3 (syn-2-azido-1,3,4-triacetoxybutane) in a single analysis and thus facilitated the precise control of the reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.