ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Nucleosides, XXXV1) Synthesis, Properties, and Reactivity of Lumazine 5-Oxide RibosidesVarious lumazine-1-mono- and -1,3-diribosides (1-6) have been converted by H2O2-oxidation in trifluoroacetic acid nto the corresponding 5-oxides 7-12. Deacylation led to free 1-(β-D-ribo-furanosyl)lumazine 5-oxide (13) and its 6, 7-dimethyl- (14) and 6, 7-diphenyl derivative (15), respectively. Treatment of the acylated lumazine riboside 5-oxides 7, 11, and 12 with acetyl chloride in TFA yielded the corresponding 6-chloro derivatives 16-18. 17 was deblocked to 6-chloro-1-(β-D-ribofuranosyl)lumazine (19) and 11 showed an interesting reaction on treatment with methanolic HCL, forming 6-methoxy-1-(β-D-ribofuranosyl)lumazine (20).
Notes:
Verschiedene Lumazin-1-mono-und-1,3-diriboside (1-6) werden durch H2O2-Oxidation in Trifluoressigsäure in die entsprechenden 5-Oxide 7-12 übergeführt. Durch Deacylierung werden das freie 1-(β-D-Ribofuranosyl)lumazin-5-oxid (13) sowie sein 6,7-Di-phenyl-Derivat (15) gewonnen. Durch Behandlung der geschützten Lumazin-ribosid-5-oxide 7, 11 und 12 mit Acetylchlorid in Trifluoressigsäure entstehen die entsprechenden 6-Chlor-Derivate 16-18. 17 wird zu 6-Chlor-1-(β-D-ribofuranosyl)lumazin (19) entacetyliert, und 11 liefert mit methanolischer HCL 6-Methoxy-1-(β-D-ribofuranosyl)lumazin (20).
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19811140229
