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.

Download
OA
Zeitschriftenaufsatz | Veröffentlicht | Englisch
Volltext vorhanden für diesen Nachweis
Autor
; ; ; ; ;
Abstract / Bemerkung
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.
Erscheinungsjahr
Zeitschriftentitel
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Band
5
ISSN
eISSN
PUB-ID

Zitieren

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).
Alle Dateien verfügbar unter der/den folgenden Lizenz(en):
Copyright Statement:
This Item is protected by copyright and/or related rights. [...]
Volltext(e)
Access Level
OA Open Access
Zuletzt Hochgeladen
1970-01-01T00:00:00Z

1 Zitation in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

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

11 References

Daten bereitgestellt von Europe PubMed Central.

YM-170320, a novel lipopeptide antibiotic inducing morphological change of colonies in a mutant of Candida tropicalis pK233.
Sugawara T, Tanaka A, Tanaka K, Nagai K, Suzuki K, Suzuki T., J. Antibiot. 51(4), 1998
PMID: 9630867
Fusaristatins A and B, two new cyclic lipopeptides from an endophytic Fusarium sp.
Shiono Y, Tsuchinari M, Shimanuki K, Miyajima T, Murayama T, Koseki T, Laatsch H, Funakoshi T, Takanami K, Suzuki K., J. Antibiot. 60(5), 2007
PMID: 17551209
Probing the proteolytic stability of beta-peptides containing alpha-fluoro- and alpha-hydroxy-beta-amino acids.
Hook DF, Gessier F, Noti C, Kast P, Seebach D., Chembiochem 5(5), 2004
PMID: 15122642
beta-Peptides: from structure to function.
Cheng RP, Gellman SH, DeGrado WF., Chem. Rev. 101(10), 2001
PMID: 11710070
The cryptophycins: their synthesis and anticancer activity.
Eggen M, Georg GI., Med Res Rev 22(2), 2002
PMID: 11857635
The outstanding metabolic stability of a 14C-labeled beta-nonapeptide in rats--in vitro and in vivo pharmacokinetic studies.
Wiegand H, Wirz B, Schweitzer A, Camenisch GP, Rodriguez Perez MI, Gross G, Woessner R, Voges R, Arvidsson PI, Frackenpohl J, Seebach D., Biopharm Drug Dispos 23(6), 2002
PMID: 12214326

Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®

Quellen

PMID: 19936267
PubMed | Europe PMC

Suchen in

Google Scholar