(4R,5R,E)-5-[(phenylsulfonyl)amino]-4-(4-methoxycarbonyl-3-butenyl)-2,2-dimethyl-1,3-dioxane | 216860-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,5R,E)-5-[(phenylsulfonyl)amino]-4-(4-methoxycarbonyl-3-butenyl)-2,2-dimethyl-1,3-dioxane
• 英文别名: methyl (E)-5-[(4R,5R)-5-(benzenesulfonamido)-2,2-dimethyl-1,3-dioxan-4-yl]pent-2-enoate
• CAS: 216860-81-0
• 化学式: C₁₈H₂₅NO₆S
• 分子量: 383.466
• InChiKey: YEVNSXWNRJFURA-SKYCBFMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  99.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4R,5R,E)-5-[(phenylsulfonyl)amino]-4-(4-methoxycarbonyl-3-butenyl)-2,2-dimethyl-1,3-dioxane 在 ruthenium trichloride 2,6-二甲基吡啶 、 盐酸 、 lithium hydroxide 、 sodium periodate 、 正丁基锂 、 对羟基联苯 、 四乙基溴化铵 、 sodium hydride 、 对甲苯磺酸 、 二异丙胺 、 N,N-二异丙基乙胺 、 2-氯-1-甲基吡啶鎓三氟甲烷磺酸盐 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 178.25h， 生成 (2R,3R,6R,7R)-3-tert-butyldimethylsilyloxy-2-carboxyl-7-ethyl-8-oxo-1-azabicyclo[4.2.0]octane
  参考文献：
  名称：

  Synthesis of Carbacephems from Serine

  摘要：

  Carbacephems have been synthesized from D-serine by two routes involving construction first of the six-membered ring followed by cyclization to give the bicyclic beta-lactam. In one route, alkylation of a lactim ether was accomplished with Ni(Acac)(2) as a catalyst. The desired R stereochemistry at the carbon corresponding to C-6 of the cephem was obtained by stereospecific hydrogenation of a vinylogous carbamate. The second route involved a stereospecific Michael cyclization to give the same C-6 stereochemistry. Closure of a piperidyl beta-amino acid intermediate common to both routes was accomplished using a modified Mukaiyama reagent found to be superior in our system to the traditional reagent. The resulting carbacephem core was stereospecifically substituted at C-7 with an ethyl or amino functionality. The ethylated intermediate was transformed into a stable enol triflate useful for the further elaboration of biologically important carbacephems.

  DOI：

  10.1021/jo980592s
• 作为产物：
  描述：

  三甲基膦酰基乙酸酯 、 N-[(4R,5R)-2,2-dimethyl-4-(3-oxopropyl)-1,3-dioxan-5-yl]benzenesulfonamide 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 23.75h， 生成 (4R,5R,Z)-5-[(phenylsulfonyl)amino]-4-(4-methoxycarbonyl-3-butenyl)-2,2-dimethyl-1,3-dioxane 、 (4R,5R,E)-5-[(phenylsulfonyl)amino]-4-(4-methoxycarbonyl-3-butenyl)-2,2-dimethyl-1,3-dioxane
  参考文献：
  名称：

  Synthesis of Carbacephems from Serine

  摘要：

  Carbacephems have been synthesized from D-serine by two routes involving construction first of the six-membered ring followed by cyclization to give the bicyclic beta-lactam. In one route, alkylation of a lactim ether was accomplished with Ni(Acac)(2) as a catalyst. The desired R stereochemistry at the carbon corresponding to C-6 of the cephem was obtained by stereospecific hydrogenation of a vinylogous carbamate. The second route involved a stereospecific Michael cyclization to give the same C-6 stereochemistry. Closure of a piperidyl beta-amino acid intermediate common to both routes was accomplished using a modified Mukaiyama reagent found to be superior in our system to the traditional reagent. The resulting carbacephem core was stereospecifically substituted at C-7 with an ethyl or amino functionality. The ethylated intermediate was transformed into a stable enol triflate useful for the further elaboration of biologically important carbacephems.

  DOI：

  10.1021/jo980592s

文献信息

• Synthesis of Carbacephems from Serine
  作者：James J. Folmer、Carles Acero、Dung L. Thai、Henry Rapoport

  DOI：10.1021/jo980592s

  日期：1998.11.1

  Carbacephems have been synthesized from D-serine by two routes involving construction first of the six-membered ring followed by cyclization to give the bicyclic beta-lactam. In one route, alkylation of a lactim ether was accomplished with Ni(Acac)(2) as a catalyst. The desired R stereochemistry at the carbon corresponding to C-6 of the cephem was obtained by stereospecific hydrogenation of a vinylogous carbamate. The second route involved a stereospecific Michael cyclization to give the same C-6 stereochemistry. Closure of a piperidyl beta-amino acid intermediate common to both routes was accomplished using a modified Mukaiyama reagent found to be superior in our system to the traditional reagent. The resulting carbacephem core was stereospecifically substituted at C-7 with an ethyl or amino functionality. The ethylated intermediate was transformed into a stable enol triflate useful for the further elaboration of biologically important carbacephems.