(3S,4S,5S)-N-(tert-butyloxycarbonyl)-5-amino-3,4-dimethyl-pyran-2-one | 1210057-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4S,5S)-N-(tert-butyloxycarbonyl)-5-amino-3,4-dimethyl-pyran-2-one
• 英文别名: tert-butyl N-[(3S,4S,5S)-4,5-dimethyl-6-oxooxan-3-yl]carbamate
• CAS: 1210057-72-9
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: DRNDQRKAUSNXGL-XHNCKOQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4S,5S)-N-(tert-butyloxycarbonyl)-5-amino-3,4-dimethyl-pyran-2-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以67%的产率得到(3R,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：

  (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

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.