Synthesis of a second-generation pseudopeptide platform

Tetrahedron Letters

Volumn 41, Issue 26, 2000, Pages 5013-5016

  Haberhauer, Gebhard ^a   Somogyi, László ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Amino acids and derivatives; Combinatorial chemistry; Macrocycles; Oxazoles; Platform

Indexed keywords

PSEUDOPEPTIDE;

ALKYLATION; ARTICLE; ENANTIOMER; HYDROGEN BOND; REACTION ANALYSIS; SYNTHESIS;

EID: 0034709593     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00796-6     Document Type: Article

References (8)

1. Kocis, P.; Issakova, O.; Sepetov, N. F.; Lebl, M. Tetrahedron Lett. 1995, 36, 6623-6626.
2. Mink, D.; Mecozzi, S.; Rebek Jr., J. Tetrahedron Lett. 1998, 39, 5709-5712.
3. Nakamura, M.; Shibata, T.; Nakane, K.; Nemoto, T.; Ojika, M.; Yamada, K. Tetrahedron Lett. 1995, 36, 5059-5062.
4. Fukuyama, T.; Xu, L. J. Am. Chem. Soc. 1993, 115, 8449-8450.
5. 4 and concentrated in vacuo. Purification was accomplished by chromatography on silica gel with AcOEt:hexane (1:2).
6. Wipf, P.; Venkatraman, S. Synlett 1997, 1, 1-10.
7. General procedure for PyBOP activated coupling: To a stirred solution of the amino building block (1 equiv.), the acid building block (1 equiv.) and N,N-diisopropylethylamine (1 equiv.) in DMF (0.06 M) was added 1.2 equiv. PyBOP at room temperature followed by slow addition of 2.8 equiv. N,N-diisopropylethylamine. Stirring was continued for 24 hours. The workup was as described above.
8. +: calculated: 611.1344; observed: 611.1342.