allyl 6α-<3'-<(tert-butyldimethylsilyl)oxy>propynyl>-6β-(trifluoromethanesulfonato)penicillinate | 147486-93-9

• 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: allyl 6α-<3'-<(tert-butyldimethylsilyl)oxy>propynyl>-6β-(trifluoromethanesulfonato)penicillinate
• 英文别名: allyl 6α-{3'-[(tert-butyldimethylsilyl)oxy]propynyl}-6β-(trifluoromethanesulfonato)penicillinate；prop-2-enyl (2S,5R,6R)-6-[3-[tert-butyl(dimethyl)silyl]oxyprop-1-ynyl]-3,3-dimethyl-7-oxo-6-(trifluoromethylsulfonyloxy)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 147486-93-9
• 化学式: C₂₁H₃₀F₃NO₇S₂Si
• 分子量: 557.684
• InChiKey: ARJXOPZWVXNMFQ-JNAXZKDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  allyl 6α-<3'-<(tert-butyldimethylsilyl)oxy>propynyl>-6β-(trifluoromethanesulfonato)penicillinate 在 copper(l) iodide 、 lithium iodide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以89%的产率得到allyl 6-methyl>vinylidene>penicillinate
  参考文献：
  名称：

  Synthesis of 6-vinylidenepenams

  摘要：

  The preparation of unique penicillin derivatives containing an exocyclic allene at the 6 position (6-vinylidenepenams) is described. The synthetic scheme utilizes 6-oxopenicillinates as intermediates which stereospecifically add acetylide anions forming propargylic alcohols. Displacement of the corresponding propargylic triflates with higher order cuprate reagents and with copper(I) halides proceeds rapidly and stereospecifically. Halogen-metal exchange of the 6-(halovinylidene)penams is described. The derived allenyl anions can be trapped by electrophiles. Conversion of selected allyl and benzhydryl esters to the corresponding carboxylic acids is described. The beta-lactamase inhibitory activity of the 6-(tert-butylvinylidene)penam sulfone is documented.

  DOI：

  10.1021/jo00058a008
• 作为产物：
  描述：

  6-氨基青霉烷酸 在 吡啶 、 高氯酸 、 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 、 sodium nitrite 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 1.58h， 生成 allyl 6α-<3'-<(tert-butyldimethylsilyl)oxy>propynyl>-6β-(trifluoromethanesulfonato)penicillinate
  参考文献：
  名称：

  Synthesis of 6-vinylidenepenams

  摘要：

  The preparation of unique penicillin derivatives containing an exocyclic allene at the 6 position (6-vinylidenepenams) is described. The synthetic scheme utilizes 6-oxopenicillinates as intermediates which stereospecifically add acetylide anions forming propargylic alcohols. Displacement of the corresponding propargylic triflates with higher order cuprate reagents and with copper(I) halides proceeds rapidly and stereospecifically. Halogen-metal exchange of the 6-(halovinylidene)penams is described. The derived allenyl anions can be trapped by electrophiles. Conversion of selected allyl and benzhydryl esters to the corresponding carboxylic acids is described. The beta-lactamase inhibitory activity of the 6-(tert-butylvinylidene)penam sulfone is documented.

  DOI：

  10.1021/jo00058a008

文献信息

• Synthesis of 6-vinylidenepenams
  作者：John D. Buynak、H. B. Borate、Grady W. Lamb、Dipti D. Khasnis、Chad Husting、Harold Isom、Upali Siriwardane

  DOI：10.1021/jo00058a008

  日期：1993.3

  The preparation of unique penicillin derivatives containing an exocyclic allene at the 6 position (6-vinylidenepenams) is described. The synthetic scheme utilizes 6-oxopenicillinates as intermediates which stereospecifically add acetylide anions forming propargylic alcohols. Displacement of the corresponding propargylic triflates with higher order cuprate reagents and with copper(I) halides proceeds rapidly and stereospecifically. Halogen-metal exchange of the 6-(halovinylidene)penams is described. The derived allenyl anions can be trapped by electrophiles. Conversion of selected allyl and benzhydryl esters to the corresponding carboxylic acids is described. The beta-lactamase inhibitory activity of the 6-(tert-butylvinylidene)penam sulfone is documented.