(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone | 159700-63-7

• 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: (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone
• CAS: 159700-63-7
• 化学式: C₁₈H₂₈N₂O₄Si
• 分子量: 364.517
• InChiKey: YFQFXVOOZDAKSN-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.87
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以91%的产率得到(3S,4S)-3-benzyloxycarbonylamino-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：

  (3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-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78%的产率得到(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-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

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.