(4R,5R)-4-(3-Hydroxypropyl)-2,2-dimethyl-5-<(phenylsulfonyl)amino>-1,3-dioxane | 151213-75-1

• 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)-4-(3-Hydroxypropyl)-2,2-dimethyl-5-<(phenylsulfonyl)amino>-1,3-dioxane
• 英文别名: (4R,5R)-5-[(phenylsulfonyl)amino]-4-(3-hydroxylpropyl)-2,2-dimethyl-1,3-dioxane；(4R,5R)-4-(3-Hydroxypropyl)-2,2-dimethyl-5-[(phenylsulfonyl)amino]-1,3-dioxane；N-[(4R,5R)-4-(3-hydroxypropyl)-2,2-dimethyl-1,3-dioxan-5-yl]benzenesulfonamide
• CAS: 151213-75-1
• 化学式: C₁₅H₂₃NO₅S
• 分子量: 329.417
• InChiKey: GPFZTSQZEUXDDD-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  93.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-(3-Hydroxypropyl)-2,2-dimethyl-5-<(phenylsulfonyl)amino>-1,3-dioxane 在 ruthenium trichloride 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium periodate 、 sodium naphthalenide 、 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 、 甲醇 、 四氯化碳 、 乙二醇二甲醚 、 phosphate buffer 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 194.5h， 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 正丁基锂 、 硼烷四氢呋喃络合物 、 L-Selectride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 77.17h， 生成 (4R,5R)-4-(3-Hydroxypropyl)-2,2-dimethyl-5-<(phenylsulfonyl)amino>-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

• Mueller, Alexander; Takyar, Dinesh K.; Witt, Sandra, Liebigs Annalen der Chemie, 1993, # 6, p. 651 - 656
  作者：Mueller, Alexander、Takyar, Dinesh K.、Witt, Sandra、Koenig, Wilfried A.

  DOI：——

  日期：——
• 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.