(2R)-N-glycyl>bornane-10,2-sultam | 175735-45-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R)-N-glycyl>bornane-10,2-sultam
• 英文别名: 2-[bis(methylsulfanyl)methylideneamino]-2,2-dideuterio-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]ethanone；2-[bis(methylsulfanyl)methylideneamino]-2,2-dideuterio-1-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]ethanone
• CAS: 175735-45-2
• 化学式: C₁₅H₂₄N₂O₃S₃
• 分子量: 378.549
• InChiKey: IXTNNTWFDQGMIN-PJIMNDSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  碘代异丁烷 、 (2R)-N-glycyl>bornane-10,2-sultam 在 六甲基磷酰三胺 作用下， 以90%的产率得到(2R,2S')-N-leucyl>bornane-10,2-sultam
  参考文献：
  名称：

  Synthesis of enantiopure α-deuteriated Boc-L-amino acids

  摘要：

  An alternative scheme for the synthesis of enantiopure alpha-deuteriated amino acids from a common intermediate is presented. Methyl bis(methylsulfanyl)methylene [2,2-H-2(2)] glycinate was prepared in a mixture of MeOD and D2O with a catalytic amount of Na2CO3 and attached to (2R)-bornane-10,2-sultam. Alkylation of the corresponding enolate provided intermediates which after careful purification were first deprotected on nitrogen and then cleaved from the auxiliary to give deuteriated alpha-amino acids of very high purity (> 99% ee and > 98% D). These were directly converted into the corresponding Boc-L-[2-H-2]-Ala, -Leu,-Phe and -(O-Bzl)Tyr derivatives, suitable for application in peptide synthesis, Boc-[2,2-H-2(2)]Gly was also prepared.

  DOI：

  10.1039/p19960000537
• 作为产物：
  描述：

  N-[二(甲硫基)亚甲基]甘氨酸甲酯 在 sodium carbonate 作用下， 以 氘代甲醇-d 、 重水 为溶剂， 反应 24.0h， 生成 (2R)-N-glycyl>bornane-10,2-sultam
  参考文献：
  名称：

  Synthesis of enantiopure α-deuteriated Boc-L-amino acids

  摘要：

  An alternative scheme for the synthesis of enantiopure alpha-deuteriated amino acids from a common intermediate is presented. Methyl bis(methylsulfanyl)methylene [2,2-H-2(2)] glycinate was prepared in a mixture of MeOD and D2O with a catalytic amount of Na2CO3 and attached to (2R)-bornane-10,2-sultam. Alkylation of the corresponding enolate provided intermediates which after careful purification were first deprotected on nitrogen and then cleaved from the auxiliary to give deuteriated alpha-amino acids of very high purity (> 99% ee and > 98% D). These were directly converted into the corresponding Boc-L-[2-H-2]-Ala, -Leu,-Phe and -(O-Bzl)Tyr derivatives, suitable for application in peptide synthesis, Boc-[2,2-H-2(2)]Gly was also prepared.

  DOI：

  10.1039/p19960000537

文献信息

• Synthesis of enantiopure α-deuteriated Boc-<scp>L</scp>-amino acids
  作者：Yiannis Elemes、Ulf Ragnarsson

  DOI：10.1039/p19960000537

  日期：——

  An alternative scheme for the synthesis of enantiopure alpha-deuteriated amino acids from a common intermediate is presented. Methyl bis(methylsulfanyl)methylene [2,2-H-2(2)] glycinate was prepared in a mixture of MeOD and D2O with a catalytic amount of Na2CO3 and attached to (2R)-bornane-10,2-sultam. Alkylation of the corresponding enolate provided intermediates which after careful purification were first deprotected on nitrogen and then cleaved from the auxiliary to give deuteriated alpha-amino acids of very high purity (> 99% ee and > 98% D). These were directly converted into the corresponding Boc-L-[2-H-2]-Ala, -Leu,-Phe and -(O-Bzl)Tyr derivatives, suitable for application in peptide synthesis, Boc-[2,2-H-2(2)]Gly was also prepared.