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Reaction of 1‐(2′,3′‐epoxy‐β‐ D ‐lyxofuranosyl)uracil with hydrogen fluoride. The unexpected formation of 1‐(3′‐fluoro‐3′‐deoxy‐β‐ D ‐ribofuranosyl)uracil
Author(s) -
Misra Hemant K.,
Gati Wendy P.,
Knaus Edward E.,
Wiebe Leonard I.
Publication year - 1984
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.5570210327
Subject(s) - chemistry , uracil , fluoride , hydrogen fluoride , epoxy , hydrogen , medicinal chemistry , stereochemistry , organic chemistry , inorganic chemistry , biochemistry , dna
Abstract Reaction of 1‐(2′,3′‐epoxy‐β‐ D ‐lyxofuranosyl)uracil ( 1 ) with hydrogen fluoride afforded 3′‐fluoro‐3′‐deoxyarabinouridine ( 2 , 13%) and 3′‐fluoro‐3′‐deoxyuridine ( 3 , 11%). The structure of 3 was assigned from spectrometric data and confirmed by an unambiguous synthesis from 2′,5′‐di‐ O ‐trityl‐2,3′‐anhydrouridine ( 5 ) and hydrogen fluoride.