(R)-4-(allyloxy)-3-(tert-butoxycarbonylamino)butanoic acid | 1135149-00-6

• 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: (R)-4-(allyloxy)-3-(tert-butoxycarbonylamino)butanoic acid
• 英文别名: Boc-O-allyl-β-serine；(3R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-prop-2-enoxybutanoic acid
• CAS: 1135149-00-6
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: PHVBAQHSJLKGCY-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-4-(allyloxy)-3-(tert-butoxycarbonylamino)butanoic acid 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 以91%的产率得到(2R)-1-carboxy-3-(prop-2-en-1-yloxy)propan-2-aminium trifluoroacetate
  参考文献：
  名称：

  The synthesis of Fmoc-O-allyl β-serine

  摘要：

  Two concise routes for the synthesis of the title amino acid have been developed. The first route employs Seebach's general approach [Seebach, D.; Lelais, G.; Micuch, P.; Josien-Lefebvre, D.; Rossi, F. Helv. Chim. Acta 2004, 87, 3131] with Arndt Eistert homologation of Boc-alpha-allyl alpha-serine as the key process. The second route employs an approach using Boc-alpha-aspartic acid as a starting material [Salzmann, T.N.; Ratcliffe, R.W.; Christensen, B.G.; Bouffard, F.A.J Am. Chem. Soc. 1980, 102, 6163; Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron. Lett. 1991, 32, 923] with a selective palladium-catalysed O-allylation [Haight, A.R: Stoner, EJ.; Peterson, MJ.: Grover, V.K.J. Org. Chem. 2003, 68, 8092] as key processes. These two routes are evaluated for their relative efficiency and safety. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.022
• 作为产物：
  描述：

  benzyl (R)-4-(allyloxy)-3-(tert-butoxycarbonylamino)-butanoate 在 lithium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以98%的产率得到(R)-4-(allyloxy)-3-(tert-butoxycarbonylamino)butanoic acid
  参考文献：
  名称：

  The synthesis of Fmoc-O-allyl β-serine

  摘要：

  Two concise routes for the synthesis of the title amino acid have been developed. The first route employs Seebach's general approach [Seebach, D.; Lelais, G.; Micuch, P.; Josien-Lefebvre, D.; Rossi, F. Helv. Chim. Acta 2004, 87, 3131] with Arndt Eistert homologation of Boc-alpha-allyl alpha-serine as the key process. The second route employs an approach using Boc-alpha-aspartic acid as a starting material [Salzmann, T.N.; Ratcliffe, R.W.; Christensen, B.G.; Bouffard, F.A.J Am. Chem. Soc. 1980, 102, 6163; Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron. Lett. 1991, 32, 923] with a selective palladium-catalysed O-allylation [Haight, A.R: Stoner, EJ.; Peterson, MJ.: Grover, V.K.J. Org. Chem. 2003, 68, 8092] as key processes. These two routes are evaluated for their relative efficiency and safety. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.022

文献信息

• The synthesis of Fmoc-O-allyl β-serine
  作者：Ylva Bergman、Marisa Ciampini、Sania Jalal、Helen Rachel Lagiakos、Marie-Isabel Aguilar、Patrick Perlmutter

  DOI：10.1016/j.tetasy.2008.12.022

  日期：2008.12

  Two concise routes for the synthesis of the title amino acid have been developed. The first route employs Seebach's general approach [Seebach, D.; Lelais, G.; Micuch, P.; Josien-Lefebvre, D.; Rossi, F. Helv. Chim. Acta 2004, 87, 3131] with Arndt Eistert homologation of Boc-alpha-allyl alpha-serine as the key process. The second route employs an approach using Boc-alpha-aspartic acid as a starting material [Salzmann, T.N.; Ratcliffe, R.W.; Christensen, B.G.; Bouffard, F.A.J Am. Chem. Soc. 1980, 102, 6163; Rodriguez, M.; Llinares, M.; Doulut, S.; Heitz, A.; Martinez, J. Tetrahedron. Lett. 1991, 32, 923] with a selective palladium-catalysed O-allylation [Haight, A.R: Stoner, EJ.; Peterson, MJ.: Grover, V.K.J. Org. Chem. 2003, 68, 8092] as key processes. These two routes are evaluated for their relative efficiency and safety. (C) 2008 Elsevier Ltd. All rights reserved.