Synthesis of 1-(3-deoxy-beta-D-psicofuranosyl)uracil and related compounds.
Year: 1974
Type: article
Abstract: D-Fructose affords on treatment with cyanamide 2-amino-beta-D-fructofuro[2',3':3,4]-oxazoline which is not isolated but transformed directly by the reaction with ethyl propiolate into O(2,3)-anhydro-2-[beta-D-fructofuranosyl]uracil. This compound is benzoylated to the 1',4',6'-tri-O-benzoyl derivative by the action of benzoyl cyanide and triethylamine. On treatment with hydrogen chloride/dimethylformamide, the latter intermediate is converted to the 1-[1,4,6-tri-O-benzoyl-3-chloro-3-deoxy-beta-D-psicofuranosyl]uracil 1',4',5'-tribenzoate from which the title nucleoside derivative is obtained by methanolysis.
Source: PubMed Central
Author: A Holý
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W44580619