2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids

Nahrwold M, Stoncius A, Penner A, Neumann B, Stammler H-G, Sewald N (2009)
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 5.

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Novel procedures have been developed to condense benzaldehyde effectively with beta-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral beta-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of functionalised beta(2)-amino acids containing acid-labile protected side chains. Diastereoselective alkylation of the tetrahydropyrimidinone is followed by a chemoselective two step degradation of the heterocycle to release the free beta(2)-amino acid. In the course of this study, an L-asparagine derivative was condensed with benzaldehyde and subsequently converted to orthogonally protected (R)-beta(2)-homoaspartate.
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BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
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Nahrwold M, Stoncius A, Penner A, Neumann B, Stammler H-G, Sewald N. 2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2009;5.
Nahrwold, M., Stoncius, A., Penner, A., Neumann, B., Stammler, H. - G., & Sewald, N. (2009). 2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 5. doi:10.3762/bjoc.5.43
Nahrwold, M., Stoncius, A., Penner, A., Neumann, B., Stammler, H. - G., and Sewald, N. (2009). 2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 5.
Nahrwold, M., et al., 2009. 2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 5.
M. Nahrwold, et al., “2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids”, BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 5, 2009.
Nahrwold, M., Stoncius, A., Penner, A., Neumann, B., Stammler, H.-G., Sewald, N.: 2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 5, (2009).
Nahrwold, Markus, Stoncius, Arvydas, Penner, Anna, Neumann, Beate, Stammler, Hans-Georg, and Sewald, Norbert. “2-Phenyl-tetrahydropyrimidine-4(1H)-ones - cyclic benzaldehyde aminals as precursors for functionalised beta(2)-amino acids”. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 5 (2009).
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Orthogonally protected thiazole and isoxazole diamino acids: an efficient synthetic route.
Butler JD, Coffman KC, Ziebart KT, Toney MD, Kurth MJ., Chemistry 16(30), 2010
PMID: 20623732

3 References

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Beta(2)/beta(3)-di- and alpha/beta(3)-tetrapeptide derivatives as potent agonists at somatostatin sst(4) receptors.
Nunn C, Rueping M, Langenegger D, Schuepbach E, Kimmerlin T, Micuch P, Hurth K, Seebach D, Hoyer D., Naunyn Schmiedebergs Arch. Pharmacol. 367(2), 2003
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