ISSN:
0170-2041
Keywords:
Uridine-5′-phosphonates, 2′,5′-dideoxy-
;
D-erythro-Pentofuranose-5-phosphonates, 2,5-dideoxy-
;
Arbuzov reaction
;
Human immunodeficiency virus
;
Herpes simplex virus
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Methyl 2,5-dideoxy-5-iodo-3-O-pivaloyl-D-erythro-pentofur-anoside (5) was synthesized from 2-deoxy-D-ribose and treated with triethyl phosphite to give the phosphonate 6. Reaction of 6 with silylated 2,4-dihydroxypyrimidine 7 in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst afforded nucleoside phosphonates 8 and 9 which were deprotected with C2H5ONa in ethanol to give the diethyl 2′,5′-dideoxyuridine-5′-phosphonate 10 and its α-anomer 11. No activity was found for the nucleosides 8-11 against HIV or HSV-1.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199219920124
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