1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-2-((S)-hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-2-((S)-hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
CAS No.:476490-60-5
Molecular Formula:C₁₆H₁₈N₂O₇
Molecular Weight:350.328
Hs Code.:

Synonyms:1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-2-((S)-hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

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Chemical Property of 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-2-((S)-hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

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Technology Process of 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-2-((S)-hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

There total 5 articles about 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-2-((S)-hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

: 476490-59-2
1-[(2R,3R,3aS,9aR)-3-Hydroxy-2-((S)-hydroxy-phenyl-methyl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl]-1H-pyrimidine-2,4-dione

: 476490-60-5
1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-2-((S)-hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.333333h;
DOI:10.1021/jo020266j

Reference yield:

: 288103-31-1
1-((2S,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-oxo-2-phenylselanyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione

: 476490-60-5
1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-2-((S)-hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / N,N-diisopropylethylamine / dimethylformamide / 0.33 h / 20 °C

2: 76 percent / SmI₂; O₂ / tetrahydrofuran / 1 h / -78 °C

3: 93 percent / NaBH₄ / methanol / 0.5 h / 0 °C

4: 100 percent / H₂ / 10percent Pd/C / methanol / 40 h / 20 °C / atmospheric pressure

5: 74 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

With sodium tetrahydroborate; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; oxygen; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo020266j

Reference yield:

: 476490-34-3
3-N-benzyloxymethyl-1-[1-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-erythro-2-pentosulofuranosyl]uracil

: 476490-60-5
1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-2-((S)-hydroxy-phenyl-methyl)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / SmI₂; O₂ / tetrahydrofuran / 1 h / -78 °C

2: 93 percent / NaBH₄ / methanol / 0.5 h / 0 °C

3: 100 percent / H₂ / 10percent Pd/C / methanol / 40 h / 20 °C / atmospheric pressure

4: 74 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

With sodium tetrahydroborate; samarium diiodide; tetrabutyl ammonium fluoride; hydrogen; oxygen; 10percent Pd/C; In tetrahydrofuran; methanol;
DOI:10.1021/jo020266j