(3S,4R)-trans-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one | 301533-10-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4R)-trans-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• 英文别名: (3S,4R)-trans-1-(p-anisyl)-3-azido-4[(S)-2',2'-dimethyl-1',3'-dioxalan-4'-yl]-azetidin-2-one；(3S,4R)-3-azido-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(4-methoxyphenyl)azetidin-2-one
• CAS: 301533-10-8
• 化学式: C₁₅H₁₈N₄O₄
• 分子量: 318.332
• InChiKey: VDKDFDANZWORNP-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  62.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R)-trans-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 在 硫化氢 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到trans-(3R,4S)-1-(4-methoxyphenyl)-3-amino-4-<(1'S)-1',2'-O-isopropylideneethyl>-2-azetidinone
  参考文献：
  名称：

  Studies on lactams. 81. Enantiospecific synthesis and absolute configuration of substituted .beta.-lactams from D-glyceraldehyde acetonide

  摘要：

  DOI：

  10.1021/jo00253a013
• 作为产物：
  描述：

  (3R,4R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-1-(4-methoxyphenyl)azetidin-2-one 在 4-二甲氨基吡啶 、 叠氮化锂 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,4R)-trans-1-(p-anisyl)-3-azido-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
  参考文献：
  名称：

  Polyhydroxy Amino Acid Derivatives via β-Lactams Using Enantiospecific Approaches and Microwave Techniques

  摘要：

  Enantiospecific synthesis has been developed for alpha-hydroxy beta-lactams of predictable absolute configuration starting with readily available carbohydrates, Stereospecific approaches and microwave assisted chemical reactions have been utilized for the preparation of these 3-hydroxy-2-azetidinones and their conversion to natural or non-natural enantiomeric forms of intermediates for gentosamine, 6-epilincosamine, gamma-hydroxythreonine, and polyoxamic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00410-5

文献信息

• WAGLE, DILIP R.;GARAI, CHANDRA;MONTELEONE, MICHAEL G.;BOSE, AJAY K., TETRAHEDRON LETT., 29,(1988) N 14, 1649-1652
  作者：WAGLE, DILIP R.、GARAI, CHANDRA、MONTELEONE, MICHAEL G.、BOSE, AJAY K.

  DOI：——

  日期：——
• Polyhydroxy Amino Acid Derivatives via β-Lactams Using Enantiospecific Approaches and Microwave Techniques
  作者：Ajay K Bose、Bimal K Banik、Chandra Mathur、Dilip R Wagle、Maghar S Manhas

  DOI：10.1016/s0040-4020(00)00410-5

  日期：2000.7

  Enantiospecific synthesis has been developed for alpha-hydroxy beta-lactams of predictable absolute configuration starting with readily available carbohydrates, Stereospecific approaches and microwave assisted chemical reactions have been utilized for the preparation of these 3-hydroxy-2-azetidinones and their conversion to natural or non-natural enantiomeric forms of intermediates for gentosamine, 6-epilincosamine, gamma-hydroxythreonine, and polyoxamic acid. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Studies on lactams. 81. Enantiospecific synthesis and absolute configuration of substituted .beta.-lactams from D-glyceraldehyde acetonide
  作者：Dilip R. Wagle、Chandra Garai、Julian Chiang、Michael G. Monteleone、Barbara E. Kurys、Timothy W. Strohmeyer、Vinod R. Hegde、Maghar S. Manhas、Ajay K. Bose

  DOI：10.1021/jo00253a013

  日期：1988.9