(2R,3R,6R)-6-methoxycarbonylmethyl-3-tert-butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-1-phenylsulfonylpiperidine | 216860-85-4

• 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,6R)-6-methoxycarbonylmethyl-3-tert-butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-1-phenylsulfonylpiperidine
• 英文别名: methyl 2-[(2R,5R,6R)-1-(benzenesulfonyl)-5-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]piperidin-2-yl]acetate
• CAS: 216860-85-4
• 化学式: C₂₇H₄₉NO₆SSi₂
• 分子量: 571.926
• InChiKey: RBZYIYBYBUXVIP-GMKZXUHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  90.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3R,6R)-6-methoxycarbonylmethyl-3-tert-butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-1-phenylsulfonylpiperidine 在 lithium hydroxide 、 对羟基联苯 、 四乙基溴化铵 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 38.0h， 生成 (2R,3R,6R)-6-carboxymethyl-3-tert-butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethylpiperidine
  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 吡啶 、 2,6-二甲基吡啶 、 盐酸 、 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 双(三甲基硅烷基)氨基钾 、 L-Selectride 、 sodium hydride 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 261.92h， 生成 (2R,3R,6R)-6-methoxycarbonylmethyl-3-tert-butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-1-phenylsulfonylpiperidine
  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