1-[(2R,3aS,7S,7aS)-7-Hydroxy-4-(2,2,2-trifluoro-acetyl)-octahydro-furo[3,2-b]pyridin-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Base Information

Chemical Name:1-[(2R,3aS,7S,7aS)-7-Hydroxy-4-(2,2,2-trifluoro-acetyl)-octahydro-furo[3,2-b]pyridin-2-yl]-5-methyl-1H-pyrimidine-2,4-dione
CAS No.:246538-38-5
Molecular Formula:C₁₄H₁₆F₃N₃O₅
Molecular Weight:363.293
Hs Code.:

Synonyms:1-[(2R,3aS,7S,7aS)-7-Hydroxy-4-(2,2,2-trifluoro-acetyl)-octahydro-furo[3,2-b]pyridin-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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Chemical Property of 1-[(2R,3aS,7S,7aS)-7-Hydroxy-4-(2,2,2-trifluoro-acetyl)-octahydro-furo[3,2-b]pyridin-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

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Technology Process of 1-[(2R,3aS,7S,7aS)-7-Hydroxy-4-(2,2,2-trifluoro-acetyl)-octahydro-furo[3,2-b]pyridin-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

There total 1 articles about 1-[(2R,3aS,7S,7aS)-7-Hydroxy-4-(2,2,2-trifluoro-acetyl)-octahydro-furo[3,2-b]pyridin-2-yl]-5-methyl-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:

: 52450-18-7
3'-amino-3'-deoxythymidine

: 246538-38-5
1-[(2R,3aS,7S,7aS)-7-Hydroxy-4-(2,2,2-trifluoro-acetyl)-octahydro-furo[3,2-b]pyridin-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 14 steps

1: 87 percent / Na₂CO₃ / 1 h / 20 °C

2: 79 percent / DMSO; DCC; TFA / pyridine / 4 h / 20 °C

3: Zn / tetrahydrofuran / 20 h / 40 °C

4: AgNO₃; pyridine / 24 h / 50 °C

5: LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

6: H₂ / 10 percent Pd/C / 20 °C

7: Et₃N / dimethylformamide / 3 h / 20 °C

8: 99 percent / pyridine / 5 h / 20 °C

9: 90 percent / PPTs / CH₂Cl₂ / 5 h / 20 °C

10: 86 percent / TBAF; AcOH / tetrahydrofuran / 15 h / 20 °C / pH 6

11: 100 percent / pyridine / 0.5 h / 20 °C

12: 69 percent / DMAP / 20 h / 40 °C

13: 76 percent / Et₃N / CH₂Cl₂ / 3 h / 20 °C

14: 100 percent / aq. AcOH / 5 h / 20 °C

With pyridine; dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium carbonate; silver nitrate; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; zinc; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Oxidation / 3: Condensation / 4: Etherification / 5: Reduction / 6: Hydrogenolysis / 7: Acylation / 8: Etherification / 9: Etherification / 10: desilylation / 11: mesylation / 12: Cyclization / 13: Acylation / 14: Hydrolysis;
DOI:10.1016/S0040-4039(99)01205-8

Reference yield: 89.0%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 246538-38-5
1-[(2R,3aS,7S,7aS)-7-Hydroxy-4-(2,2,2-trifluoro-acetyl)-octahydro-furo[3,2-b]pyridin-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 246538-39-6
1-[(2R,3aS,7S,7aS)-7-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-4-(2,2,2-trifluoro-acetyl)-octahydro-furo[3,2-b]pyridin-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: With pyridine; silver trifluoromethanesulfonate; at 50 ℃; for 24h;
DOI:10.1016/S0040-4039(99)01205-8

Reference yield:

: 246538-38-5
1-[(2R,3aS,7S,7aS)-7-Hydroxy-4-(2,2,2-trifluoro-acetyl)-octahydro-furo[3,2-b]pyridin-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

: 1-{(2R,3aS,7S,7aS)-7-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-octahydro-furo[3,2-b]pyridin-2-yl}-5-methyl-1H-pyrimidine-2,4-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / AgOTf; pyridine / 24 h / 50 °C

2: 95 percent / NH₄OH / methanol / 2 h / 20 °C

With pyridine; ammonium hydroxide; silver trifluoromethanesulfonate; In methanol; 1: Etherification / 2: Hydrolysis;
DOI:10.1016/S0040-4039(99)01205-8