(6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-methylsulfanyl-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester | 59780-00-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-methylsulfanyl-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• 英文别名: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[[[(1,1-dimethylethoxy)carbonyl]amino]phenylacetyl]amino]-3-(methylthio)-8-oxo-, diphenylmethyl ester, 5-oxide, [6R-[6I+/-,7I(2)(R*)]]-；benzhydryl (6R,7R)-7-[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetyl]amino]-3-methylsulfanyl-5,8-dioxo-5λ4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 59780-00-6
• 化学式: C₃₄H₃₅N₃O₇S₂
• 分子量: 661.8
• InChiKey: IKOCXSDESVNJJP-LKNRKEMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  131.11
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-methylsulfanyl-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 在 苯甲醚 、 间氯过氧苯甲酸 、 三氟乙酸 、 三氯化磷 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 生成 (6R)-7t-((R)-2-amino-2-phenyl-acetylamino)-3-methanesulfonyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  参考文献：
  名称：

  Neue ?-Lactam-Antibiotika. �ber die Funktionalisierung der Cephem-3-Stellung mittels Schwefel oder Stickstoff. Modifikationen von Antibiotika, 13. Mitteilung

  摘要：

  New β‐lactam antibiotics. Functionalisation of the cephem 3‐position with sulfur or nitrogen bearing substituentsThe tosylate sulfoxides or mesylates derived from the 3‐hydroxy‐ceph‐3‐em esters 1a, b reacted with thiols to give 3‐thioethers which were converted into the microbiologically active acids 7a, c, 8a, c 9c, and 13c by known procedures. The 3‐methylsulfonyl‐derivative 17c was prepared from 6b. The synthesis of the 3‐acylamino‐ceph‐3‐em‐4‐carboxylic acids 23c and 24c is reported.

  DOI：

  10.1002/hlca.19750580824
• 作为产物：
  描述：

  (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3,5ξ,8-trioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid benzhydryl ester 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (6R)-7t-((R)-2-tert-butoxycarbonylamino-2-phenyl-acetylamino)-3-methylsulfanyl-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
  参考文献：
  名称：

  Neue ?-Lactam-Antibiotika. �ber die Funktionalisierung der Cephem-3-Stellung mittels Schwefel oder Stickstoff. Modifikationen von Antibiotika, 13. Mitteilung

  摘要：

  New β‐lactam antibiotics. Functionalisation of the cephem 3‐position with sulfur or nitrogen bearing substituentsThe tosylate sulfoxides or mesylates derived from the 3‐hydroxy‐ceph‐3‐em esters 1a, b reacted with thiols to give 3‐thioethers which were converted into the microbiologically active acids 7a, c, 8a, c 9c, and 13c by known procedures. The 3‐methylsulfonyl‐derivative 17c was prepared from 6b. The synthesis of the 3‐acylamino‐ceph‐3‐em‐4‐carboxylic acids 23c and 24c is reported.

  DOI：

  10.1002/hlca.19750580824