(3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one | 138332-40-8

• 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: (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one
• 英文别名: (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-(benzoylthio)-2-azetidinone；(3S,4R)-4-benzoylthio-3-[(1R)-(1-tert-butyldimethylsiloxy)ethyl]-azetidin-2-one；S-[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] benzenecarbothioate
• CAS: 138332-40-8
• 化学式: C₁₈H₂₇NO₃SSi
• 分子量: 365.569
• InChiKey: NWZOJCHCJACYRE-IVMMDQJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one 在 三乙胺 、 亚磷酸三乙酯 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 11.17h， 生成 prop-2-enyl (5R,6S)-6-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-7-oxo-3-phenyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
  参考文献：
  名称：

  Structure-activity relationships of penem antibiotics: Crystallographic structures and implications for their antimicrobial activities

  摘要：

  Twelve closely related crystal structures of the penem derivatives revealed a characteristic short contact of the oxygen atom in the C2 side-chains with the S1 atom. The side-chain conformations of the crystal structures showed a good correlation with the antimicrobial activity. In particular, the penems which show high antimicrobial activity have similar torsion angles for S1-C2-C1'-C2', suggesting that the disposition of the C2' atom would be important for binding to penicillin-interacting enzymes. Two conformations of the C6 hydroxyethyl group were observed in the crystal structures. Of those two, the conformation with a larger torsion angle (delta = 179.2 degrees) is deduced to be the enzyme-bound conformation in the Michaelis complex. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00073-4
• 作为产物：
  描述：

  硫代苯甲酸 、 (3S,4R)-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-4-phenylthioazetidin-2-one 以 甲苯 、 乙腈 为溶剂， 生成 (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one
  参考文献：
  名称：

  Copper catalyzed process for producing 4-substituted azetidinone

  摘要：

  生产4-取代氮杂环丙酮衍生物的工艺，该衍生物由以下通用公式\x9bIII!表示：##STR1##（其中OR是保护羟基，Y是烷基，烷氧基，硅烷氧基，氨基甲酰氧基，氨基，取代或未取代芳香族基或取代或未取代杂环基，n是0或1的整数，但当Y是烷氧基，硅烷氧基，氨基甲酰氧基或氨基时，n不能表示0），其特征在于在有机溶剂中，在铜化合物的存在下，将以下通用公式\x9bI!表示的2-氮杂环丙酮衍生物：##STR2##（其中OR如上定义，X是烷基或取代或未取代芳香族基）与以下通用公式\x9bII!表示的硫代羧酸发生反应：HSCO--(CH.sub.2).sub.n --Y\x9bII!（其中Y和n分别如上定义）。

  公开号：

  US05808055A1

文献信息

• An Efficient Synthesis of 4-Heterofunction-Substituted 3-(1-Hydroxy)ethylazetidin-2-ones from 3-(1-Hydroxy)ethyl-4-phenylsulfinylazetidin-2-one by Reaction with Silylated Heteronucleophiles.
  作者：Yasuyuki KITA、Norio SHIBATA、Naoki YOSHIDA、Takashi TOHJO

  DOI：10.1248/cpb.40.1733

  日期：——

  3-(1-tert-Butyldimethylsiloxy)ethyl-4-sulfinylazetidin-2-one was reacted with silylated N-, S-, O-, and P-nucleophiles in the presence of a catalytic amount of ZnI2 to give the corresponding trans-4-heterofunction-substituted azetidin-2-ones in high yelids.

  在催化量 ZnI2 的存在下，3-(1-叔丁基二甲基硅氧基)乙基-4-亚磺酰基氮杂环丁烷-2-酮与硅烷化的 N-、S-、O-和 P-亲核物发生反应，得到相应的反式-4-杂环丁烷-2-酮高倍率化合物。
• A novel substitution reaction of 4-sulfinylazetidin-2-one with silylated heteronucleophiles: an efficient synthesis of 4-heterofunction substituted 3-(1-hydroxy)ethylazetidin-2-ones
  作者：Yasuyuki Kita、Norio Shibata、Naoki Yoshida、Takashi Tohjo

  DOI：10.1016/s0040-4039(00)79927-8

  日期：1991.5

  4-Sulfinylazetidin-2-one was reacted with silylated heteronucleophiles in the presence of a catalytic amount of zinc iodide to give the corresponding trans-4-heterofunction substituted azetidin-2-ones in high yields.
• Copper-assisted substitution reaction for phenylthio group of a 4-phenylthioazetidinone derivative
  作者：Tetsuo Shimamoto、Hidekazu Inoue、Takuro Yoshida、Rie Tanaka、Takashi Nakatsuka、Masaji Ishiguro

  DOI：10.1016/s0040-4039(00)78210-4

  日期：1994.8

  The phenylthio group of 4-phenylthioazetidinone (1) was readily substituted with copper(I) salts of carboxylates, thiocarboxylates, and copper(I) enolates of malonates and beta-ketoesters to give synthetic intermediates (3 and 4) for penem and carbapenem antibiotics.