1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3-oxo]propyl-azetidin-2-one | 146467-05-2

• 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: 1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3-oxo]propyl-azetidin-2-one
• 英文别名: (4S,5R)-5-[(2R,3S)-1-benzyl-4-oxo-3-phenylmethoxyazetidin-2-yl]-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 146467-05-2
• 化学式: C₂₃H₂₅NO₅
• 分子量: 395.455
• InChiKey: AFQPAZUBSCCWBS-CGXNFDGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3-oxo]propyl-azetidin-2-one 在 palladium on activated charcoal ruthenium trichloride 、 sodium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 、 lithium aluminium tetrahydride 、 ammonium formate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 四氯化碳 、 二氯甲烷 、 乙二醇 、 乙腈 为溶剂， 反应 11.6h， 生成 (-)-polyoxamic 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：

  cis-1-benzyl-3S-benzyloxy-4R-[1'R,2'S,3'R,4'-di-O-isopropylidene]butyl-azetidin-2-one 在 sodium periodate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 61.25h， 生成 1-benzyl-3S-benzyloxy-4R-[1'R,2'S-O-isopropylidene-3-oxo]propyl-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

• Enantioselective total synthesis of (2S,3R,4R)-d-xylo-phytosphingosine from substituted azetidin-2-one
  作者：Ganesh Pandey、Dharmendra Kumar Tiwari

  DOI：10.1016/j.tetlet.2009.02.050

  日期：2009.7

  Enantiomerically pure (2S,3R,4R)-d-xylo phytosphingosine is synthesized in 36% overall yield in seven steps from known β-lactam (8) derived from d-mannitol triacetonide.

  对映体纯的（2 S，3 R，4 R）-d-二甲苯基植物神经鞘氨醇分七步从七个已知的衍生自d-甘露醇三丙酮化物的β-内酰胺（8）中以36％的总产率合成。
• Studies on lactams. 89. Versatile .beta.-lactam synthons: enantiospecific synthesis of (-)-polyoxamic acid
  作者：Bimal K. Banik、Maghar S. Manhas、Ajay K. Bose

  DOI：10.1021/jo00054a007

  日期：1993.1

  An optically pure cis-alpha-hydroxy beta-lactam of predictable absolute configuration prepared from readily available D-mannitol has been utilized for the synthesis of the non-natural enantiomer of polyoxamic acid through a series of stereospecific reactions.