(3S,4R)-1-Benzyl-4-((2R,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-methoxy-azetidin-2-one | 301532-87-6

• 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)-1-Benzyl-4-((2R,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-methoxy-azetidin-2-one
• CAS: 301532-87-6
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: IKOZRLZPYKDKEX-WGJBLAJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.49
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  88.46
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3S,4R)-1-Benzyl-4-((2R,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-methoxy-azetidin-2-one 在 ruthenium trichloride 、 sodium periodate 作用下， 以 乙腈 为溶剂， 反应 30.0h， 以37%的产率得到(2S,3S)-1-Benzyl-3-methoxy-4-oxo-azetidine-2-carboxylic acid
  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
• 作为产物：
  描述：

  N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine 在 甲醇 、 三聚氯氰 、 碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (3S,4R)-1-Benzyl-4-((2R,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-methoxy-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