[(2R,3S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-butyl]-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-(diethoxy-phosphoryl)-acetic acid tert-butyl ester | 201472-44-8

• 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: [(2R,3S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-butyl]-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-(diethoxy-phosphoryl)-acetic acid tert-butyl ester
• 英文别名: tert-butyl 2-[(2R,3S)-2-[4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxybutyl]-3-(1,3-dioxoisoindol-2-yl)-4-oxoazetidin-1-yl]-2-diethoxyphosphorylacetate
• CAS: 201472-44-8
• 化学式: C₃₁H₄₉N₂O₁₀PSi
• 分子量: 668.797
• InChiKey: BERBYXPJUIIWQL-IHPLILTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-butyl]-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-(diethoxy-phosphoryl)-acetic acid tert-butyl ester 在 sodium sulfide 、 重铬酸吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 甲基肼 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.42h， 生成 (6R,7S)-7-Amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of an Important 3-(Hydroxymethyl)carbacephalosporin

  摘要：

  Carbacephalosporins have gained much attention as important antibacterial agents. Recently, 3-(hydroxymethyl)carbacephalosporins have been linked to quinolones for the production of multifunctional antibiotics. A short, practical asymmetric total synthesis of carbacephalosporin 3, suitable for conjugating to other chemical moieties, is reported. The synthesis was achieved by Mitsunobu cyclization of dipeptide 12, prepared from L-erythro-anti-beta-hydroxy-alpha-amino acid 11, and subsequent Horner-Wadsworth-Emmons cyclization of ketone 16.

  DOI：

  10.1021/jo971772p
• 作为产物：
  描述：

  二乙基膦酰基乙酸叔丁酯 在 4-二甲氨基吡啶 、 四氧化锇 、 二苯基膦酰羟胺 、 sodium hydride 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N-甲基吗啉氧化物 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 40.0h， 生成 [(2R,3S)-2-[4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-butyl]-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-1-yl]-(diethoxy-phosphoryl)-acetic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of an Important 3-(Hydroxymethyl)carbacephalosporin

  摘要：

  Carbacephalosporins have gained much attention as important antibacterial agents. Recently, 3-(hydroxymethyl)carbacephalosporins have been linked to quinolones for the production of multifunctional antibiotics. A short, practical asymmetric total synthesis of carbacephalosporin 3, suitable for conjugating to other chemical moieties, is reported. The synthesis was achieved by Mitsunobu cyclization of dipeptide 12, prepared from L-erythro-anti-beta-hydroxy-alpha-amino acid 11, and subsequent Horner-Wadsworth-Emmons cyclization of ketone 16.

  DOI：

  10.1021/jo971772p

文献信息

• Asymmetric Total Synthesis of an Important 3-(Hydroxymethyl)carbacephalosporin
  作者：Mark G. Stocksdale、Savithri Ramurthy、Marvin J. Miller

  DOI：10.1021/jo971772p

  日期：1998.2.1

  Carbacephalosporins have gained much attention as important antibacterial agents. Recently, 3-(hydroxymethyl)carbacephalosporins have been linked to quinolones for the production of multifunctional antibiotics. A short, practical asymmetric total synthesis of carbacephalosporin 3, suitable for conjugating to other chemical moieties, is reported. The synthesis was achieved by Mitsunobu cyclization of dipeptide 12, prepared from L-erythro-anti-beta-hydroxy-alpha-amino acid 11, and subsequent Horner-Wadsworth-Emmons cyclization of ketone 16.