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The synthesis of some 5‐methoxypyrimidine nucleosides
Author(s) -
Stout M. G.,
Robins R. K.
Publication year - 1972
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570090314
Subject(s) - chemistry , alkylation , amination , stereochemistry , diastereomer , organic chemistry , catalysis
The synthesis of 5‐methoxyuridine ( 3 ), 5‐methoxycytidine ( 6 ), 1‐(2‐deoxy‐β‐D‐ erythro pento‐furanosyl)‐5‐methoxyuracil ( 14 ), 5‐methoxy‐1‐β‐D‐ribofuranosyl‐4‐thiopyrimidin‐2‐one ( 5 ), 1‐β‐D‐arabinofuranosyl‐5‐methoxycytosine ( 12 ), 1‐β‐D‐arabinofuranosyl‐5‐methoxyuracil ( 8 ) and 1‐β‐D‐arabinofuranosyl‐5‐methoxy‐4‐thiopyrimidin‐2‐one ( 11 ) have been accomplished. Both 3 and 14 were synthesized by alkylation of 2,4‐ bis (trimethyIsilyI)‐5‐methoxyuracil ( 1 ) with the appropriately blocked halosugars. Synthesis of the corresponding 5‐methoxy‐1‐β‐D‐arabinofuranosyl derivatives was accomplished through the intermediate 2,2 ‐anhydro‐1‐β‐D‐arabinofuranosyl‐5‐methoxyuracil ( 7 ). The cytosine and 4‐thiouracil derivatives in both the arabino‐ and ribo‐ series were prepared by thiation followed by amination.