Boc-Aib-OAllyl | 127043-33-8

• 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: Boc-Aib-OAllyl
• 英文别名: Prop-2-en-1-yl 2-{[(tert-butoxy)carbonyl]amino}-2-methylpropanoate；prop-2-enyl 2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 127043-33-8
• 化学式: C₁₂H₂₁NO₄
• mdl: MFCD24391912
• 分子量: 243.303
• InChiKey: BIQMRWVANJXYLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 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：

  Boc-Aib-OAllyl 在 三氟乙酸 作用下， 反应 0.58h， 以88%的产率得到H-Aib-OAllyl*Tfa
  参考文献：
  名称：

  PyBOP® and PyBroP: Two reagents for the difficult coupling of the α,α-dialkyl amino acid, Aib.

  摘要：

  The difficult coupling of alpha-aminoisobutyric acid (Aib) was carried out using PyBOP(R) and PyBroP in a comparative study with BOP and BroP. These reagents gave good results under simple conditions (one pot, r.t., 1 h). Coded amino acids could be coupled with Aib using PyBOP under standard conditions of peptide synthesis without racemization whereas the coupling of two Aib residues required PyBroP/DMAP. A fragment containing an Aib C-terminal could be coupled without epimerization of the penultimate residue.

  DOI：

  10.1016/s0040-4020(01)80922-4
• 作为产物：
  描述：

  氟甲酸叔丁酯 在 sodium hydroxide 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 Boc-Aib-OAllyl
  参考文献：
  名称：

  PyBOP® and PyBroP: Two reagents for the difficult coupling of the α,α-dialkyl amino acid, Aib.

  摘要：

  The difficult coupling of alpha-aminoisobutyric acid (Aib) was carried out using PyBOP(R) and PyBroP in a comparative study with BOP and BroP. These reagents gave good results under simple conditions (one pot, r.t., 1 h). Coded amino acids could be coupled with Aib using PyBOP under standard conditions of peptide synthesis without racemization whereas the coupling of two Aib residues required PyBroP/DMAP. A fragment containing an Aib C-terminal could be coupled without epimerization of the penultimate residue.

  DOI：

  10.1016/s0040-4020(01)80922-4

文献信息

• 10.1021/acs.orglett.4c02376
  作者：Petrone, David A.、Maturano, Jonathan、Herbort, James、Plasek, Erin E.、Vivaldo-Nikitovic, J. Mayeli、Sarlah, David

  DOI：10.1021/acs.orglett.4c02376

  日期：——

  allows access to a diverse array of valuable β,β-disubstituted alanine derivatives. This synthesis exhibits broad functional group tolerance, and permits efficient access to β-aryl-β-alkyl, and the more rarely reported β,β-dialkyl Ala derivatives with high yield and excellent enantioselectivity. This transformation has been exhibited on decagram quantity, and can be used to generate Fmoc amino acid derivatives

  我们报告了连续 C(sp 2 )–C(sp 3 ) Suzuki 交叉偶联不对称氢化策略的开发，该策略允许获得多种有价值的 β,β-二取代丙氨酸衍生物。该合成表现出广泛的官能团耐受性，并可以有效地获得β-芳基-β-烷基和更罕见报道的β,β-二烷基Ala衍生物，具有高产率和优异的对映选择性。这种转化已在十克数量上得到展示，并且可用于生成可用于 SPPS 的 Fmoc 氨基酸衍生物。
• FREROT, ERIC;COSTE, JACQUES;PANTALONI, ANTOINE;DUFOUR, MARIE-NOELLE;JOUIN+, TETRAHEDRON, 47,(1991) N, C. 259-270
  作者：FREROT, ERIC、COSTE, JACQUES、PANTALONI, ANTOINE、DUFOUR, MARIE-NOELLE、JOUIN+

  DOI：——

  日期：——
• PyBOP® and PyBroP: Two reagents for the difficult coupling of the α,α-dialkyl amino acid, Aib.
  作者：Eric Frérot、Jacques Coste、Antoine Pantaloni、Marie-Noëlle Dufour、Patrick Jouin

  DOI：10.1016/s0040-4020(01)80922-4

  日期：1991.1

  The difficult coupling of alpha-aminoisobutyric acid (Aib) was carried out using PyBOP(R) and PyBroP in a comparative study with BOP and BroP. These reagents gave good results under simple conditions (one pot, r.t., 1 h). Coded amino acids could be coupled with Aib using PyBOP under standard conditions of peptide synthesis without racemization whereas the coupling of two Aib residues required PyBroP/DMAP. A fragment containing an Aib C-terminal could be coupled without epimerization of the penultimate residue.