Pyrimidine Nucleosides. II. The Synthesis of Unnatural Pyrimidine Nucleosides saturated at 5, 6-Double Bond

5, 6-Dihydroxy-5, 6-dihydro-2'-deoxyuridine (IIIa) and 5, 6-dihydroxy-5, 6-dihydrouridine (IIIb) were prepared via bromination of 2'-deoxyuridine (Ia) and uridine (Ib) respectively, followed by refluxing these unstable intermediates in the neutral conditions to replace the bromo group with...

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Published inChemical & pharmaceutical bulletin Vol. 17; no. 4; pp. 650 - 652
Main Authors KANAI, TADASHI, ICHINO, MOTONOBU, KOJIMA, TAKASHI
Format Journal Article
LanguageEnglish
Published Japan The Pharmaceutical Society of Japan 1969
Japan Science and Technology Agency
Subjects
Chemical Phenomena
Chemistry
Nucleosides - chemical synthesis
Pyrimidines - chemical synthesis
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Summary:5, 6-Dihydroxy-5, 6-dihydro-2'-deoxyuridine (IIIa) and 5, 6-dihydroxy-5, 6-dihydrouridine (IIIb) were prepared via bromination of 2'-deoxyuridine (Ia) and uridine (Ib) respectively, followed by refluxing these unstable intermediates in the neutral conditions to replace the bromo group with the hydroxyl group. In the case of cytidine, however, the 5, 6-dihydroxy-5, 6-dihydro compound was not obtained by the same procedure as used for preparation of IIIa and IIIb from Ia and Ib.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.17.650