Protection of Carboxyl Groups

作者: E. Haslam

DOI: 10.1007/978-1-4684-7218-9_5

关键词: Substrate (chemistry)Group (periodic table)ChemistryMalonic acidOrder (group theory)Combinatorial chemistryHexamethylphosphoric TriamideMolecule

摘要: In synthesis it is often desirable to protect a carboxyl function in order bring about specific reactions elsewhere the molecule and subsequently regenerate original group under conditions which do not affect other sensitive groups substrate. An elegant example of this principle shown route formation 6-aminopenicillamic acid (5) from intermediate (1) [1, 2] general penicillins due Sheehan Henery-Logan [3]. practice, as example, most easily blocked form an ester. Table 5.1, at end Chapter, lists those esters have been widely employed or properties appear be suitable for task. Open image new window

参考文章(134)
Stanley R. Sandler, Wolf Karo, Organic Functional Group Preparations ,(1972)
F. Elsinger, J. Schreiber, A. Eschenmoser, Notiz über die Selektivität der Spaltung von Carbonsäuremethylestern mit Lithiumjodid Helvetica Chimica Acta. ,vol. 43, pp. 113- 118 ,(1960) , 10.1002/HLCA.19600430116
J. A. Barltrop, P. J. Plant, P. Schofield, Photosensitive protective groups Chemical Communications (London). pp. 822- 823 ,(1966) , 10.1039/C19660000822
P. M. Bryant, R. H. Moore, P. J. Pimlott, G. T. Young, 780. Amino-acids and peptides. Part XIV. Further studies on the synthesis of aspartyl-peptides Journal of The Chemical Society (resumed). pp. 3868- 3873 ,(1959) , 10.1039/JR9590003868
Kurt Bodenbenner, Über spirocyclische Orthoester Justus Liebigs Annalen der Chemie. ,vol. 623, pp. 183- 190 ,(1959) , 10.1002/JLAC.19596230121
R. E. Bowman, W. D. Fordham, 614. Experiments on the synthesis of carbonyl compounds. Part V. β-Keto-esters and -nitriles Journal of The Chemical Society (resumed). pp. 2758- 2760 ,(1951) , 10.1039/JR9510002758
R. Camble, R. Garner, G. T. Young, Amino-acids and peptides. Part XXX. Facilitation of peptide synthesis by the use of 4-picolyl esters for carboxy-group protection Journal of the Chemical Society C: Organic. pp. 1911- 1916 ,(1969) , 10.1039/J39690001911
R. Schwyzer, B. Iselin, M. Feurer, Über aktivierte Ester. I. Aktivierte Ester der Hippursäure und ihre Umsetzungen mit Benzylamin Helvetica Chimica Acta. ,vol. 38, pp. 69- 79 ,(1955) , 10.1002/HLCA.19550380109