ISSN:
0021-8383
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Syntheses of 1-(β-D-Arbinofuranosyl)-pyrimidinesNew synthetic methods of 1-(β-D-arabinofuranosyl)-pyrimidines are described. 1-(β-D-arabinofuranosyl)-uracil, 1-(β-D-arabinofuranosyl)-5-fluorouracil, 1-(β-D-arabinofuranosyl)-thymine, and 1-(β-D-arabinofuranosyl)-cytosine can be obtained in a high yield by the splitting of the anhydrobond in 2,2′-anhydropyrimidines in dipolar aprotic solvents, such as HMPT, DMF, and DMSO, respectively, in the presence of activated elemental copper.Unlike the formation of cyclopyrimidiens ribonucleosides are directly transformed to the corresponding arabinofuranosyl derivatives by the reaction with diphenylcarbonate and NaHCO3 in the presence of copper. The reaction proceeds probably via an intermediate formation of the cycloproduct. Further aspects on the mechanism are described.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19833250307
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