(3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone | 113599-60-3

• 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-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone
• 英文别名: benzyl N-[(2S,3S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-oxoazetidin-3-yl]carbamate
• CAS: 113599-60-3
• 化学式: C₁₈H₂₈N₂O₄Si
• 分子量: 364.517
• InChiKey: NHXIASGPEODKPB-CABCVRRESA-N

物化性质

• 沸点：
  503.8±50.0 °C(predicted)
• 密度：
  1.11±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone 在 palladium on activated charcoal 氢氧化钾 、 四丁基溴化铵 、 氢气 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成 allyl 2-<(3S,4S)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-oxo-3-tritylamino-1-azetidinyl>-3-oxopropanoate
  参考文献：
  名称：

  An examination of O-2-isocephems as orally absorbable antibiotics

  摘要：

  The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.

  DOI：

  10.1021/jm00401a020
• 作为产物：
  描述：

  benzyl ((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(hydroxymethyl)-4-oxoazetidin-3-yl)carbamate 在 4-二甲氨基吡啶 、 potassium fluoride 、 dipotassium hydrogenphosphate 、 dipotassium peroxodisulfate 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 8.0h， 生成 (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone
  参考文献：
  名称：

  An examination of O-2-isocephems as orally absorbable antibiotics

  摘要：

  The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.

  DOI：

  10.1021/jm00401a020

文献信息

• Design, synthesis and antibacterial activities of a series of new 2-oxaisocephems
  作者：Jianbo Wu、Xueying Wu、Fan Lei、Huajie Yuan、Li Hai、Yong Wu

  DOI：10.1016/j.bmcl.2012.06.040

  日期：2012.8

  A series of 2-oxaisocephems with a thio-substituted methyl group at the 3-position and a [2-(5-amino-1,2,4-thiadizol-3-yl)-2-(Z)-alkoxyimino]acetamido moiety at 7-position were synthesized and tested for their antibacterial activities. The analogs 17c and 17f have well-balanced potency and significantly enhanced activity as compared with the reference compound ceftazidime. (C) 2012 Elsevier Ltd. All rights reserved.
• XIYAMA, TAMEHDZIRO;KAVABATA, TAKEHO
  作者：XIYAMA, TAMEHDZIRO、KAVABATA, TAKEHO

  DOI：——

  日期：——
• MASTALERZ, HAROLD;MENARD, MARCEL;VINET, VIVIANNE;DESIDERIO, JAMES;FUNG-TO+, J. MED. CHEM., 31,(1988) N 6, 1190-1196
  作者：MASTALERZ, HAROLD、MENARD, MARCEL、VINET, VIVIANNE、DESIDERIO, JAMES、FUNG-TO+

  DOI：——

  日期：——
• An examination of O-2-isocephems as orally absorbable antibiotics
  作者：Harold Mastalerz、Marcel Menard、Vivianne Vinet、James Desiderio、Joan Fung-Tomc、Robert Kessler、Yuan Tsai

  DOI：10.1021/jm00401a020

  日期：1988.6

  The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.