2009
DOI: 10.1021/jo802599v
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Synthesis of Deoxytetrahydrouridine

Abstract: The α-hydroxyamido functionality of 2′-deoxytetrahydrouridine (dTHU) makes this seemingly simple and generally useful compound difficult to obtain. Reported synthetic strategies produce extremely poor yields and multiple products, and full characterization data is not available. Described herein is a two-step approach for synthesizing dTHU in increased yields and purity; stability concerns are also addressed. Catalytic reduction (5% Rh/alumina) of 2′-deoxyuridine, followed by reduction with sodium borohydride … Show more

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Cited by 4 publications
(2 citation statements)
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“…Thus, they can be prepared by reduction of the corresponding aromatic counterparts. Several methods can be used for this transformation (photoreduction, borohydride reduction, hydrogenation), but hydrogenation in the presence of rhodium [276] or ruthenium [277] catalysts is particularly useful. This approach has been used for the syntheses of dihydropyrimidine-2,4(1H,3H)-diones 54 spiro-fused at the 5-position to pyrrolidines, [278] or the 1,3,6-trisubstituted dihydropyrimidine-2,4(1H,3H)-diones 55 [279] or 56 (Scheme 106).…”
Section: Methods 8: Cycloadditionsmentioning
confidence: 99%
“…Thus, they can be prepared by reduction of the corresponding aromatic counterparts. Several methods can be used for this transformation (photoreduction, borohydride reduction, hydrogenation), but hydrogenation in the presence of rhodium [276] or ruthenium [277] catalysts is particularly useful. This approach has been used for the syntheses of dihydropyrimidine-2,4(1H,3H)-diones 54 spiro-fused at the 5-position to pyrrolidines, [278] or the 1,3,6-trisubstituted dihydropyrimidine-2,4(1H,3H)-diones 55 [279] or 56 (Scheme 106).…”
Section: Methods 8: Cycloadditionsmentioning
confidence: 99%
“…For the preparation of fluorinated analogues of 5, we used a procedure similar to the one described previously by the Sturla group for the synthesis of 2′-deoxytetrahydrouridine. 17 As illustrated in Scheme 1, compound 2 served as a starting material for the synthesis of 2′-deoxy-2′,2′-difluorotetrahydrouridine. Rhodium-catalyzed hydrogenation of 2 gave 2′deoxy-2′,2′-difluorodihydrouridine 6.…”
Section: ■ Chemistrymentioning
confidence: 99%