N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine | 301532-85-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine
• CAS: 301532-85-4
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: YQHUEZJGQXWMAX-SMJFVJSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.28
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 N-(benzyl)-4-(methyl-2,3-O-isopropylidene-4b-D-ribopento-1,4-furanoside)methylene-imine
  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

• Practical Synthesis of α-Amino Acid <i>N</i>-Carboxy Anhydrides of Polyhydroxylated α-Amino Acids from β-Lactam Frameworks. Model Studies toward the Synthesis of Directly Linked Peptidyl Nucleoside Antibiotics
  作者：Claudio Palomo、Mikel Oiarbide、Aitor Esnal、Aitor Landa、José I. Miranda、Anthony Linden

  DOI：10.1021/jo980354x

  日期：1998.8.1

  A straightforward method for the synthesis of polyhydroxylated alpha-amino acid N-carboxy anhydrides (NCAs) is described as the means by which short peptide segments comprised of a polyhydroxylated chain are easily affordable. The entire sequence lies in the preparation of nonracemic 3-hydroxy beta-lactams through the highly diastereoselective Staudinger reaction of hydroxyketene equivalents with chiral

  描述了一种简单的合成多羟基化α-氨基酸N-羧基酸酐（NCA）的方法，这种方法可轻松负担得起由多羟基化链组成的短肽段。整个序列在于通过以下方法制备非外消旋的3-羟基β-内酰胺：羟基烯酮当量与手性α-氧化醛衍生的亚胺的高度非对映选择性的Staudinger反应，然后由TEMPO自由基辅助环扩展为相应的NCA，随后与α-偶联的肽偶联氨基酸酯。该方法已应用于合成从氨基甲酰基聚草酰胺酸，一些甘氨酸，以及C（2）对称羟基氨基酸衍生的短肽段。