(3S,4R)-4-[(2R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(4,4-dimethyl-2-sulfanylidene-1,3-oxazolidin-3-yl)-1-oxobutan-2-yl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]azetidin-2-one | 183052-34-8

• 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-[(2R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(4,4-dimethyl-2-sulfanylidene-1,3-oxazolidin-3-yl)-1-oxobutan-2-yl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]azetidin-2-one
• CAS: 183052-34-8
• 化学式: C₂₆H₅₀N₂O₅SSi₂
• 分子量: 558.93
• InChiKey: BEPKGGNPQVXXHR-UAFMIMERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R)-4-[(2R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(4,4-dimethyl-2-sulfanylidene-1,3-oxazolidin-3-yl)-1-oxobutan-2-yl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]azetidin-2-one 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 72.0h， 生成 diethyl 2-[[(2R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-1-(2-oxo-2-prop-2-enoxyacetyl)azetidin-2-yl]butanoyl]sulfanylmethyl]propanedioate
  参考文献：
  名称：

  A New Synthesis of 1β-Alkylcarbapenems Utilizing Eschenmoser Sulfide Contraction of the Novel Thiazinone Intermediates

  摘要：

  Novel syntheses of the 1,beta-alkylcarbapenems were achieved on the basis of Eschenmoser sulfide contraction via the new bicyclic 1,3-thiazinone intermediates. 1,3-Thiazinones 7, 16, and 25 were effectively prepared from thioesters 5 and 22 using a C4-S bond formation process. The sulfide contraction reactions were performed by treatment of 7, 16, and 25 with base (NaH or KO-t-Bu) in the presence of triphenylphosphine to generate the corresponding carbapenem enolate 12, 17, and 26, which were trapped by (PhO)(2)POCl followed by the reaction with mercaptans to afford carbapenems 10a, 10b, 19, and 28, respectively.

  DOI：

  10.1021/jo960764q
• 作为产物：
  描述：

  4-乙酰氧基氮杂环丁酮 、 在 N-乙基哌啶 、 tin(II) trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以66%的产率得到(3S,4R)-4-[(2R)-4-[tert-butyl(dimethyl)silyl]oxy-1-(4,4-dimethyl-2-sulfanylidene-1,3-oxazolidin-3-yl)-1-oxobutan-2-yl]-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]azetidin-2-one
  参考文献：
  名称：

  A New Synthesis of 1β-Alkylcarbapenems Utilizing Eschenmoser Sulfide Contraction of the Novel Thiazinone Intermediates

  摘要：

  Novel syntheses of the 1,beta-alkylcarbapenems were achieved on the basis of Eschenmoser sulfide contraction via the new bicyclic 1,3-thiazinone intermediates. 1,3-Thiazinones 7, 16, and 25 were effectively prepared from thioesters 5 and 22 using a C4-S bond formation process. The sulfide contraction reactions were performed by treatment of 7, 16, and 25 with base (NaH or KO-t-Bu) in the presence of triphenylphosphine to generate the corresponding carbapenem enolate 12, 17, and 26, which were trapped by (PhO)(2)POCl followed by the reaction with mercaptans to afford carbapenems 10a, 10b, 19, and 28, respectively.

  DOI：

  10.1021/jo960764q

文献信息

• A New Synthesis of 1β-Alkylcarbapenems Utilizing Eschenmoser Sulfide Contraction of the Novel Thiazinone Intermediates
  作者：Osamu Sakurai、Tsuyoshi Ogiku、Masami Takahashi、Masahito Hayashi、Takeshi Yamanaka、Hiroshi Horikawa、Tameo Iwasaki

  DOI：10.1021/jo960764q

  日期：1996.1.1

  Novel syntheses of the 1,beta-alkylcarbapenems were achieved on the basis of Eschenmoser sulfide contraction via the new bicyclic 1,3-thiazinone intermediates. 1,3-Thiazinones 7, 16, and 25 were effectively prepared from thioesters 5 and 22 using a C4-S bond formation process. The sulfide contraction reactions were performed by treatment of 7, 16, and 25 with base (NaH or KO-t-Bu) in the presence of triphenylphosphine to generate the corresponding carbapenem enolate 12, 17, and 26, which were trapped by (PhO)(2)POCl followed by the reaction with mercaptans to afford carbapenems 10a, 10b, 19, and 28, respectively.