(2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide | 216860-70-7

• 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: (2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide
• 英文别名: (4aR,8aR)-5-(benzenesulfonyl)-2,2-dimethyl-4a,7,8,8a-tetrahydro-4H-[1,3]dioxino[5,4-b]pyridin-6-one
• CAS: 216860-70-7
• 化学式: C₁₅H₁₉NO₅S
• 分子量: 325.386
• InChiKey: USMHDJWJVFZVML-CHWSQXEVSA-N

物化性质

• 熔点：
  176-178 °C
• 沸点：
  464.016±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.282±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide 在 咪唑 、 盐酸 、 sodium naphthalenide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 89.5h， 生成 (2R,3R)-6-oxo-3-tert-butyldimethylsilyloxy-2-(tert-butyldimethylsilyloxymethyl)piperidine
  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：

  N-(苯基磺酰基)-D-丝氨酸 在 ruthenium trichloride 4-二甲氨基吡啶 、 sodium periodate 、 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 L-Selectride 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 四氯化碳 、 phosphate buffer 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 181.17h， 生成 (2R,3R)-6-oxo-3-hydroxy-2-hydroxymethyl-1-phenylsulfonylpiperidine acetonide
  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.