(3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one

• 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,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one
• 英文别名: (4-nitrophenyl)methyl 4-[(2R,3S)-1-[tert-butyl(dimethyl)silyl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]-3-oxobutanoate
• 化学式: C₂₈H₄₆N₂O₇Si₂
• 分子量: 578.853
• InChiKey: HNPDDIQHIZOWOL-RZPHLTDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one 生成 (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one
  参考文献：
  名称：

  CHRISTENSEN, BURTON GRANT;RATCLIFFE, RONALD WILLIAM;SALZMAN, THOMAS NORSE

  摘要：

  DOI：
• 作为产物：
  描述：

  (3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-hydroxypropyl]azetidin-2-one 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxopropyl]azetidin-2-one
  参考文献：
  名称：

  Process for the preparation of 1-carbapenems and intermediates via

  摘要：

  揭示了一种从L-天冬氨酸经过中间体II和III全合成1-卡巴比林类抗生素(I)的过程：其中R为氢、药用可接受的酯基或盐阳离子，或易于去除的阻断基；R.sup.6和R.sup.7等独立地选自包括氢、烷基、烯基、芳基和芳基烷基在内的群；R.sup.1'为氢或保护基；R.sup.a、R.sup.b和R.sup.c独立地选自烷基、芳基和芳基烷基。

  公开号：

  US04309346A1

文献信息

• A mild method for the conversion of proipiolic esters to β-keto esters. application to the formal total synthesis of (±)-thienamycin
  作者：Masakatsu Shibasaki、Atsushi Nishida、Shiro Ikegami

  DOI：10.1016/s0040-4039(00)88437-3

  日期：——

  An extremely mild method for the transformation of propiolic esters to β-keto esters via thiol addition is reported, including its successful application to the synthesis of (±)-thienamycin.

  据报道，通过硫醇加成将丙酸酯转化为β-酮酸酯的极其温和的方法，包括其成功地用于合成（±）-硫霉素的方法。
• Process for the preparation of thienamycin and intermediates
  申请人：Merck & Co., Inc.

  公开号：US04290947A1

  公开（公告）日：1981-09-22

  Disclosed is a process for the total synthesis of thienamycin from L-aspartic acid via intermediate III: ##STR1## R=H, blocking group or salt cation.

  披露了一种从L-天冬氨酸经过中间体III全合成噻氨霉素的过程：##STR1## R=H，阻断基或盐阳离子。
• Process for the preparation of 1-carbapenems and intermediates via
  申请人：Merck & Co., Inc.

  公开号：US04309346A1

  公开（公告）日：1982-01-05

  Disclosed is a process for the total synthesis of 1-carbapenem antibiotics (I) from L-aspartic acid via intermediates II and III: ##STR1## wherein R is hydrogen, a pharmaceutically acceptable ester moiety or salt cation, or a readily removable blocking group; R.sup.6 and R.sup.7 are, inter alia, independently selected from the group consisting of hydrogen, alkyl, alkenyl, aryl and aralkyl; R.sup.1' is hydrogen or a protecting group; and R.sup.a, R.sup.b and R.sup.c are independently selected from alkyl, aryl and aralkyl.

  揭示了一种从L-天冬氨酸经过中间体II和III全合成1-卡巴比林类抗生素(I)的过程：其中R为氢、药用可接受的酯基或盐阳离子，或易于去除的阻断基；R.sup.6和R.sup.7等独立地选自包括氢、烷基、烯基、芳基和芳基烷基在内的群；R.sup.1'为氢或保护基；R.sup.a、R.sup.b和R.sup.c独立地选自烷基、芳基和芳基烷基。
• A formal total synthesis of thienamycin from 4-propargyl-2-azetidinone.
  作者：ATSUSHI NISHIDA、MASAKATSU SHIBASAKI、SHIRO IKEGAMI

  DOI：10.1248/cpb.34.1434

  日期：——

  A mild and efficient method for the conversion of propiolic esters to β-keto esters was developed. Initially, propiolic esters were converted to β-phenylthio-α, β-unsaturated esters, which were treated with N-bromoacetamide in an aqueous solvent followed by reductive debromination with an aqueous solution of sodium sulfite, affording β-keto esters in good yields. Using this new method, a formal total synthesis of (±)-thienamycin from 4-propargyl-2-azetidinone was accomplished.

  研究人员开发了一种温和、高效的方法，用于将丙炔酯转化为 β-酮酯。首先，将丙炔酯转化为 β-苯硫基-α，β-不饱和酯，然后在水性溶剂中用 N-溴乙酰胺处理，再用亚硫酸钠水溶液进行还原脱溴，从而以良好的收率得到 β-酮酯。利用这种新方法，从 4-丙炔基-2-氮杂环丁酮正式全合成了(±)-噻吩霉素。
• CHRISTENSEN, BURTON GRANT;RATCLIFFE, RONALD WILLIAM;SALZMAN, THOMAS NORSE
  作者：CHRISTENSEN, BURTON GRANT、RATCLIFFE, RONALD WILLIAM、SALZMAN, THOMAS NORSE

  DOI：——

  日期：——