N-Ethylcarboxamide von lyxo-Purinnucleosiden

Aus 2,3-O-Isopropylidenlyxuronsaure-methylester (1a) wurde was 1 α-Chlor-1-desoxy-N-ethyl-2,3-O-isopropylidenlyxuronamid (2d) hergestellt. Schmelzkondensation mit silyliertem 6-Chlor- und 2,6-Dichlorpurin (4a, b) lieferte im wesentlichen die N-9-verknupften α- und β-konfigurierten N-Ethyl-lyxo-purinnucleosidcarboxamide 5a, b und 6a, b. Die Struktur der erhaltenen Nucleoside wurde 1H- und 13C-NMR-spektroskopisch gesichert. N-Ethyl lyxo Purine Nucleoside Carboxamides Methyl-2,3-O-isopropylidene lyxuronate (1a) was transformed into 1 α-chloro-1-desoxy-N-ethyl-2,3-O-isopropylidene lyxuronamide (2d). Direct molten state condensation of 2d with silylated 6-chloro- and 2,6-dichloropurine (4a, b) yields mainly N-ethyl-N-9-purinyl nucleoside carboxamides with α and β-configuration (5a, b and 6a, b). The structure of these compounds was established from 1H- and 13C-NMR data.

[1]  R. R. Schmidt,et al.  Glycosylhydrazine, 5. Aufbauende Synthese der 5‐Säureamid‐Derivate von Pyrazol‐, Pyrazolo[3,4‐d]pyrimidin‐ und 1H‐1,2,4‐Triazol‐nucleosiden , 1981 .

[2]  R. R. Schmidt,et al.  Riburon- und Lyxuronpurinnucleosid-Derivate – Synthese, Trennung und Struktursicherung der verschiedenen Verknüpfungsisomeren , 1980 .

[3]  R. R. Schmidt,et al.  Spezifische Synthese von Nucleosid‐5′‐carbonsäure‐Derivaten mit Pyrimidinen als heterocyclische Base , 1980 .

[4]  R. R. Schmidt,et al.  Funktionelle D-Lyxuronsäure-Derivate aus D-Mannose , 1979 .

[5]  R. Schmidt,et al.  A convenient preparation of 2,3-unsaturated N-galactosyl derivatives , 1979 .

[6]  R. Schinazi,et al.  Synthesis and biological activities of some uronic acids, uronates, uronamides, and urononitriles of pyrimidine nucleosides. , 1978, Journal of medicinal chemistry.

[7]  M. Maccoss,et al.  Nucleic acid related compounds. 26. A "geometry-only" method for determining the anomeric configuration of nucleosides based on the H-1' NMR signal of cyclic alpha and beta 3',5'-mononucleotides1. , 1977, Journal of the American Chemical Society.

[8]  P. Somani,et al.  CARDIOVASCULAR EFFECTS OF NUCLEOSIDE ANALOGS , 1975, Annals of the New York Academy of Sciences.

[9]  A. A. Akhrem,et al.  Synthesis of uracil nucleosides of D-xyluronic acid derivatives. , 1975, Carbohydrate Research.

[10]  J. B. Petersen,et al.  Catalytic oxidation of two ribonucleosides in the 5'-position. , 1975, Nucleic acids research.

[11]  H. Fritz,et al.  Synthese und Struktur von Inosin‐5′‐carbonsäure und Derivaten , 1970 .

[12]  R. Schmidt,et al.  Synthese 5′-modifizierter Adenosinderivate , 1968 .

[13]  M. Sela,et al.  Antibodies elicited with conjugates of nucleosides with synthetic polypeptides. , 1967, Biochimica et biophysica acta.

[14]  M. Wolfrom,et al.  NUCLEOSIDES OF D-GLUCURONIC ACID AND OF D-GLUCOFURANOSE AND D-GALACTOFURANOSE. , 1965, The Journal of organic chemistry.