6β-hydroxypenicillanic acid benzyl ester | 15139-36-3

• 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: 6β-hydroxypenicillanic acid benzyl ester
• 英文别名: benzyl 6β-hydroxypenicillanate；6β-hydroxy-penicillanic acid benzyl ester；Benzyl-6β-hydroxypenicillanat；benzyl (2S,5R,6R)-6-hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 15139-36-3
• 化学式: C₁₅H₁₇NO₄S
• 分子量: 307.37
• InChiKey: XZNVUJIUQOYXIH-NTZNESFSSA-N

物化性质

• 沸点：
  496.7±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6β-hydroxypenicillanic acid benzyl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 6β-hydroxy-1β-oxo-1λ4-penicillanic acid benzyl ester
  参考文献：
  名称：

  Roets; Vlietinck; Vanderhaeghe, Journal of the Chemical Society. Perkin transactions I, 1976, # 6, p. 704 - 710

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 在 sodium tetrahydroborate 、 乙酸酐 作用下， 以 甲醇 、 乙醇 、 二甲基亚砜 为溶剂， 生成 6β-hydroxypenicillanic acid benzyl ester
  参考文献：
  名称：

  Roets; Vlietinck; Vanderhaeghe, Journal of the Chemical Society. Perkin transactions I, 1976, # 6, p. 704 - 710

  摘要：

  DOI：

文献信息

• Carbon and oxygen analogs of penicillin
  申请人：Massachusetts Institute of Technology

  公开号：US04143046A1

  公开（公告）日：1979-03-06

  In accordance with this invention, it has been found that carbon and oxygen analogs of 6.beta.-aminopenicillanic acid and biologically active derivatives thereof can be formed from esters of 6-oxopenicillanic acid. For example, 6.beta.-phenoxyacetoxypenicillanic acid -- an oxygen analog of penicillin V and 6.beta.-phenoxyacetylmethylpenicillanic acid -- a carbon analog of penicillin V, may be formed from an ester of 6-oxopenicillanate. The ester of 6-oxopenicillanic acid is formed by a diiospropyl carbodiimide/dimethyl sulfoxide oxidation of the corresponding ester of 6.alpha.-hydroxypenicillanic acid. The oxygen analogs are formed by reducing the ester of 6-oxopenicillanic acid to the corresponding 6.beta.-hydroxypenicillanate and then forming the desired analog by acylation. The carbon analogs are formed by a Wittig reaction of the ester of 6-oxopenicillanic acid with a suitable acylmethylenetriphenylphosphorane followed by saturation of the newly formed double bond and removal of the protective ester group.

  根据这项发明，发现可以从6-氧代青霉素酸的酯类形成6.beta.-氨基青霉素酸和其生物活性衍生物的碳和氧类似物。例如，6.beta.-苯氧乙酰氧基青霉素酸--青霉素V的氧类似物和6.beta.-苯氧乙酰甲基青霉素酸--青霉素V的碳类似物，可以从6-氧代青霉素酸的酯类形成。6-氧代青霉素酸的酯类是通过对应的6.alpha.-羟基青霉素酸的酯类经过二异丙基碳二亚胺/二甲基亚砜氧化形成的。氧类似物是通过将6-氧代青霉素酸的酯类还原为相应的6.beta.-羟基青霉素酸酯类，然后通过酰化形成所需的类似物。碳类似物是通过将6-氧代青霉素酸的酯类与适当的酰亚甲基三苯基膦烯进行Wittig反应，然后饱和新形成的双键并去除保护酯基而形成的。
• Penicillin derivatives, process for their preparation and pharmaceutical compositions containing certain of these compounds
  申请人：BEECHAM GROUP PLC

  公开号：EP0013617A1

  公开（公告）日：1980-07-23

  This invention relates to a process for the preparation of certain penicillin derivatives which are useful as β-lactamase inhibitors. The compounds which may be prepared by the process of this invention have formula (I), or a pharmaceutically acceptable salt or ester thereof: wherein R represents hydrogen, halogen, C1-6alkylthio, C1-6alkyl or alkyl substituted with phenyl, carboxy, C1-6alkoxycarbonyl, hydroxyorC1-6alkylthio, and n is zero, 1 or 2. In addition certain of the compounds produced by the process of the invention are novel compounds.

  本发明涉及一种制备某些青霉素衍生物的工艺，这些衍生物可用作β-内酰胺酶抑制剂。可通过本发明工艺制备的化合物具有式（I）或其药学上可接受的盐或酯： 其中R代表氢、卤素、C1-6烷硫基、C1-6烷基或被苯基、羧基、C1-6烷氧基羰基、羟基或C1-6烷硫基取代的烷基，n为0、1或2。此外，本发明工艺生产的某些化合物是新型化合物。
• HARBRIDGE, J. B.;DENERLEY, P. M.
  作者：HARBRIDGE, J. B.、DENERLEY, P. M.

  DOI：——

  日期：——
• SHEEHAN, J. C.;LO, Y. S.
  作者：SHEEHAN, J. C.、LO, Y. S.

  DOI：——

  日期：——
• JOSIDA, TESAKU;TANAKA, KIESI;TODO, JODZO;FUKUOKA, JOSIKADZU;TAI, MASARU;S+
  作者：JOSIDA, TESAKU、TANAKA, KIESI、TODO, JODZO、FUKUOKA, JOSIKADZU、TAI, MASARU、S+

  DOI：——

  日期：——