Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate | 143159-88-0

• 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: Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate
• 英文别名: Diphenylmethyl 2-[(3R, 4R)-4-[(benzothiazol-2-yl)dithio1-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-2,3-butadienoate
• CAS: 143159-88-0
• 化学式: C₃₅H₂₇N₃O₅S₃
• 分子量: 665.814
• InChiKey: LRGZCRYOIYWDSH-LXANVCGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  顺式-1-溴-1-丙烯 、 Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate 生成 Diphenylmethyl (7S,6R)-7-(phenoxyacetamido)-3-(Z)-propenyl-3-cephem-4-carboxylate 、
  参考文献：
  名称：

  A Novel Approach to Cephalosporins From Allenylazetidinones: A New Cyclization Strategy via Tandem Cuprate Addition-Sulfenylation

  摘要：

  An efficient approach to the synthesis of 3-substituted cephems bearing carbon-based substituents of choice at the C(3) position from inexpensive penicillins is described. The strategy involves the synthesis of an allenylazetidinone from penicillin sulfoxide followed by the addition of an organocuprate at low temperature. Organocuprates undergo 1,4-conjugate addition at the central allenic carbon of the allenylazetidinone to form a carbon-carbon bond which is followed by ring closure via an intramolecular sulfenylation reaction. The chemistry has been applied to the synthesis of a variety of 3-substituted cephems bearing substituents such as alkyl, cycloalkyl, aryl, alkenyl, and allyl. Precursors to the synthesis of important antibiotics, i.e., Cefadroxil, Cefixime, and Cefzil, are also available from this novel approach. The methodology is not limited to carbon-based 3-substituted cephems, but provides access to some 3-norcephalosporins as well.

  DOI：

  10.1021/jo00096a045
• 作为产物：
  描述：

  Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-3-<(trifluoromethanesulfonyl)oxy>-2-butenoate 在 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以90%的产率得到Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate
  参考文献：
  名称：

  A Novel Approach to Cephalosporins From Allenylazetidinones: A New Cyclization Strategy via Tandem Cuprate Addition-Sulfenylation

  摘要：

  An efficient approach to the synthesis of 3-substituted cephems bearing carbon-based substituents of choice at the C(3) position from inexpensive penicillins is described. The strategy involves the synthesis of an allenylazetidinone from penicillin sulfoxide followed by the addition of an organocuprate at low temperature. Organocuprates undergo 1,4-conjugate addition at the central allenic carbon of the allenylazetidinone to form a carbon-carbon bond which is followed by ring closure via an intramolecular sulfenylation reaction. The chemistry has been applied to the synthesis of a variety of 3-substituted cephems bearing substituents such as alkyl, cycloalkyl, aryl, alkenyl, and allyl. Precursors to the synthesis of important antibiotics, i.e., Cefadroxil, Cefixime, and Cefzil, are also available from this novel approach. The methodology is not limited to carbon-based 3-substituted cephems, but provides access to some 3-norcephalosporins as well.

  DOI：

  10.1021/jo00096a045

文献信息

• Processes for making cephems from allenylazetidinone derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US05162521A1

  公开（公告）日：1992-11-10

  This invention relates to a novel process for making a cephem of formula II from 2-(3-amino-2-oxo-azetidin-1-yl)-2,3-butadienoate of formula I. In another aspect, this invention is concerned with a process of further converting a compound of formula II into an antibacterial cephem of formula III. ##STR1## In formulae I, II and III, R.sup.1 is hydrogen, a conventional amino protecting group or an acyl group; R.sup.2 is an aromatic heterocyclic or aryl group; R.sup.3 is a conventional carboxy protecting group or --CO.sub.2 R.sup.3 taken together forms a physiologically hydrolyzable ester; and R.sup.4 is a group selected from the group consisting of C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, cyclic C.sub.3-6 alkyl, and aryl; and n is 0 or 2.

  本发明涉及一种从式I的2-(3-氨基-2-氧代-氮杂环丁烯-1-基)-2,3-丁二烯酸酯制备式II头孢菌素的新工艺。另一方面，本发明涉及一种将式II化合物进一步转化为式III抗菌头孢菌素的工艺。在式I、II和III中，R1是氢、传统的氨基保护基或酰基；R2是芳香杂环或芳基基团；R3是传统的羧基保护基或--CO2R3，二者结合形成生理可水解的酯；R4是从C1-6烷基、C2-6烯基、C2-6炔基、环状C3-6烷基和芳基组成的一种基团；n为0或2。
• A stereocontrolled synthesis of cefprozil and related cephems via allenylazetidinones
  作者：Joydeep Kant、Vittorio Farina

  DOI：10.1016/s0040-4039(00)92503-6

  日期：1992.6

  A new method for the preparation of cephalosporins bearing carbon substituents of choice at C-3 is described. The approach involves 1,4-conjugate addition of an organocuprate to an allenylazetidinone to form a carbon-carbon bond followed by ring closure via intramolecular sulfenylation reaction.