(2S,3S,4S) ethyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-2,3-dimethyl-5-oxo-pentanoate | 1210057-71-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,4S) ethyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-2,3-dimethyl-5-oxo-pentanoate
• 英文别名: tert-butyl (4S)-4-[(2S,3S)-4-ethoxy-3-methyl-4-oxobutan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 1210057-71-8
• 化学式: C₁₇H₃₁NO₅
• 分子量: 329.437
• InChiKey: UAZGNLDKKLJKSB-RWMBFGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S) ethyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-2,3-dimethyl-5-oxo-pentanoate 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以67%的产率得到(3S,4S,5S)-N-(tert-butyloxycarbonyl)-5-amino-3,4-dimethyl-pyran-2-one
  参考文献：
  名称：

  Synthetic Studies on Callipeltins: Stereoselective Syntheses of (3S,4R)-3,4-Dimethyl-L-pyroglutamic Acid and Fmoc-D-allothreonine from Serine Derivatives

  摘要：

  The non-proteinogenic amino acids contained in callipeltins, (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid and D-allothreonine, were synthesized from D- or L-serine. The stereoselective synthesis of two methyl groups of (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid was accomplished by diastereoselective hydrogenation and alkylation. Kinetic epimerization of the C-4 methyl substituent followed by Boc-deprotection with 10% TFA gave the desired (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid as a single isomer.

  DOI：

  10.3987/com-09-11834
• 作为产物：
  描述：

  (3S,4S) ethyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxo-pentanoate 、 碘甲烷 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以77%的产率得到(2S,3S,4S) ethyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-2,3-dimethyl-5-oxo-pentanoate
  参考文献：
  名称：

  Synthetic Studies on Callipeltins: Stereoselective Syntheses of (3S,4R)-3,4-Dimethyl-L-pyroglutamic Acid and Fmoc-D-allothreonine from Serine Derivatives

  摘要：

  The non-proteinogenic amino acids contained in callipeltins, (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid and D-allothreonine, were synthesized from D- or L-serine. The stereoselective synthesis of two methyl groups of (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid was accomplished by diastereoselective hydrogenation and alkylation. Kinetic epimerization of the C-4 methyl substituent followed by Boc-deprotection with 10% TFA gave the desired (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid as a single isomer.

  DOI：

  10.3987/com-09-11834

文献信息

• Synthetic Studies on Callipeltins: Stereoselective Syntheses of (3S,4R)-3,4-Dimethyl-L-pyroglutamic Acid and Fmoc-D-allothreonine from Serine Derivatives
  作者：Hiroyuki Konno、Yoko Takebayashi、Kazuto Nosaka、Kenichi Akaji

  DOI：10.3987/com-09-11834

  日期：——

  The non-proteinogenic amino acids contained in callipeltins, (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid and D-allothreonine, were synthesized from D- or L-serine. The stereoselective synthesis of two methyl groups of (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid was accomplished by diastereoselective hydrogenation and alkylation. Kinetic epimerization of the C-4 methyl substituent followed by Boc-deprotection with 10% TFA gave the desired (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid as a single isomer.