(2S,4S) 1-(benzyloxy)-3--4-<(4-methoxyphenoxy)methyl>-2-azetidinone | 159622-48-7

• 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: (2S,4S) 1-(benzyloxy)-3--4-<(4-methoxyphenoxy)methyl>-2-azetidinone
• 英文别名: (2S,4S) 1-(benzyloxy)-3-(N,N'-bis(tert-butoxycarbonyl)hydrazino)-4-[(4-methoxyphenoxy)methyl]-2-azetidinone；tert-butyl N-[(2S,3S)-2-[(4-methoxyphenoxy)methyl]-4-oxo-1-phenylmethoxyazetidin-3-yl]-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbamate
• CAS: 159622-48-7
• 化学式: C₂₈H₃₇N₃O₈
• 分子量: 543.617
• InChiKey: HXYKWYFQEWZLIV-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,4S) 1-(benzyloxy)-3--4-<(4-methoxyphenoxy)methyl>-2-azetidinone 在 吡啶 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以83%的产率得到(3S,4S) 1-(benzyloxy)-3--4-hydroxymethyl-2-azetidinone
  参考文献：
  名称：

  Microbiological enantioselective synthesis of (S) and (R) 4-(p-anisyloxy)-3-hydroxybutyrates as new chiral building blocks for the synthesis of β-lactam antibiotics

  摘要：

  Both anantiomers of 4-p-anisyloxy-3-hydroxybutanoates 4 have been prepared in high e.e. by reduction of the corresponding beta-ketoesters or beta-ketocarboxylates with immobilized fermenting baker's yeast. the utility of these new chiral building blocks in the synthesis of pharmacologically important beta-lactam antibiotics has been demonstrated.

  DOI：

  10.1016/s0040-4020(01)89309-1
• 作为产物：
  描述：

  对甲氧基苯氧乙酸 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 N,N'-羰基二咪唑 、 lithium diisopropyl amide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 40.75h， 生成 (2S,4S) 1-(benzyloxy)-3--4-<(4-methoxyphenoxy)methyl>-2-azetidinone
  参考文献：
  名称：

  Microbiological enantioselective synthesis of (S) and (R) 4-(p-anisyloxy)-3-hydroxybutyrates as new chiral building blocks for the synthesis of β-lactam antibiotics

  摘要：

  Both anantiomers of 4-p-anisyloxy-3-hydroxybutanoates 4 have been prepared in high e.e. by reduction of the corresponding beta-ketoesters or beta-ketocarboxylates with immobilized fermenting baker's yeast. the utility of these new chiral building blocks in the synthesis of pharmacologically important beta-lactam antibiotics has been demonstrated.

  DOI：

  10.1016/s0040-4020(01)89309-1

文献信息

• Microbiological enantioselective synthesis of (S) and (R) 4-(p-anisyloxy)-3-hydroxybutyrates as new chiral building blocks for the synthesis of β-lactam antibiotics
  作者：Luca Banfi、Giuseppe Cascio、Chiara Ghiron、Giuseppe Guanti、Elso Manghisi、Enrica Narisano、Renata Riva

  DOI：10.1016/s0040-4020(01)89309-1

  日期：1994.1

  Both anantiomers of 4-p-anisyloxy-3-hydroxybutanoates 4 have been prepared in high e.e. by reduction of the corresponding beta-ketoesters or beta-ketocarboxylates with immobilized fermenting baker's yeast. the utility of these new chiral building blocks in the synthesis of pharmacologically important beta-lactam antibiotics has been demonstrated.