Thio-analogues of 5,6-dihydrouridine

Skaric, V.; Gašbpert, B.; Hohnjec, Marijan

doi:10.1039/j39700002444

Cited by 5 publications

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“…We revealed that hydrogenolysis of N 3 -benzyl-2,3-O-isopropylideneuridine (5) by hydrogen transfer from cyclohexene or 1,4-cyclohexadiene in the presence of Pearlman's catalyst or 10% Pd/C did not lead to the desired 2,3-O-isopropylideneuridine (9). Instead of this, a preferential formation of N 3 -benzyluridine (10) was observed (Scheme 2).…”

Section: Resultsmentioning

confidence: 75%

“…The most striking observation was that in the presence of HCO 2 NH 4 as a hydrogen donor, [8] the catalytic transfer hydrogenolysis of N 3 -benzyl-2,3-Oisopropylideneuridine (5) proceeds with reduction of the 4,5 double bond of nucleobase with unaffected isopropylidene block. Compounds 10 [4] and 11 [9] were identified by comparison with literature data.…”

Section: Resultsmentioning

confidence: 99%

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Simultaneous Removal of Benzyl and Benzyloxycarbonyl Protective Groups in 5′-O-(2-Deoxy-α-D-Glucopyranosyl)Uridine by Catalytic Transfer Hydrogenolysis

Wandzik

Bieg

Kadela

2008

Nucleosides, Nucleotides and Nucleic Acids

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Section: Resultsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Simultaneous Removal of Benzyl and Benzyloxycarbonyl Protective Groups in 5′-O-(2-Deoxy-α-D-Glucopyranosyl)Uridine by Catalytic Transfer Hydrogenolysis

Wandzik

Bieg

Kadela

2008

Nucleosides, Nucleotides and Nucleic Acids

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References

1985

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Synthesis of 5‐Methyluridine and Its 5′‐Mercapto‐, 2‐Amino‐, and 4′,5′‐Unsaturated Analogues

Škarié

Matulié-Adamié

1980

Helvetica Chimica Acta

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The stereospecific cis-hydroxylation of 1-(2,3-dideoxy-P-~-glyceropent-2-enofuranosy1)thymine (1) into 1 -P-D-ribofuranosylthymine (2) by osmium tetroxide is described. Treatment of 2', 3'-0,O-isopropylidene-5-methyl-2,5'-anhydrouridine (8) with hydrogen sulfide or methanolic ammonia afforded 5'-deoxy-2', 3'-0, O-isopropylidene-5'-mercapto-5-methyluridine (9) and 2',3'-0,O-isopropylidene-5-methyl-isocytidine (lo), respectively. The action of ethanolic potassium hydroxide on 5'-deoxy-5'-iodo-2', 3'-0,O-isopropylidene-5-methyluridine (7) gave rise to the corresponding l-(~-deoxy-~-~-erythropent-4-enofuranosyl)5-methyluracil (13) and 2-0-ethyl-5 -methyluridine (14).The hydrogenation of 2 and its 2', 3'-0,O-isopropylidene derivative 4 over 5% Rh/A120, as catalyst generated diastereoisomers of the corresponding 5-methyl-5,6dihydrouridine (17 and 18).

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Thio-analogues of 5,6-dihydrouridine

Cited by 5 publications

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Simultaneous Removal of Benzyl and Benzyloxycarbonyl Protective Groups in 5′-O-(2-Deoxy-α-D-Glucopyranosyl)Uridine by Catalytic Transfer Hydrogenolysis

Simultaneous Removal of Benzyl and Benzyloxycarbonyl Protective Groups in 5′-O-(2-Deoxy-α-D-Glucopyranosyl)Uridine by Catalytic Transfer Hydrogenolysis

References

Synthesis of 5‐Methyluridine and Its 5′‐Mercapto‐, 2‐Amino‐, and 4′,5′‐Unsaturated Analogues

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