Thiophosphoric acid O-{3-[1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propyl} ester S-phenyl ester

Base Information

Chemical Name:Thiophosphoric acid O-{3-[1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propyl} ester S-phenyl ester
CAS No.:198822-78-5
Molecular Formula:C₂₁H₂₇N₂O₉PS
Molecular Weight:514.493
Hs Code.:

Thiophosphoric acid O-{3-[1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propyl} ester S-phenyl ester

Synonyms:Thiophosphoric acid O-{3-[1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propyl} ester S-phenyl ester

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Chemical Property of Thiophosphoric acid O-{3-[1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propyl} ester S-phenyl ester

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Technology Process of Thiophosphoric acid O-{3-[1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propyl} ester S-phenyl ester

There total 9 articles about Thiophosphoric acid O-{3-[1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propyl} ester S-phenyl ester 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:

: 84500-33-4,65499-40-3
2',3',5'-tri-O-acetyl-5-iodouridine

: 198822-78-5
Thiophosphoric acid O-{3-[1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propyl} ester S-phenyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 80 percent / Pd(PPh₃)4, CuI, triethylamine / dimethylformamide / 20 h

2: H₂ / Pd/C / ethanol / 25 h

3: 0.5 M NaOH / pyridine / 0.17 h

4: 1.) PhB(OH)2; 2.) imidazole / 1.) pyridine, 1 h; 2.) DMF, 1.5 h

5: 69 percent / 80 percent AcOH / 12 h

6: 84 percent / TMSCl / acetone / 20 h

7: 69 percent / DDS, 1H-tetrazole / pyridine / 1 h

8: (Bu₃Sn)2O / pyridine / 1 h

9: TBAF*H₂O / tetrahydrofuran / 5 h

With 1H-imidazole; 1H-tetrazole; sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; tetrabutyl ammonium fluoride; hydrogen; acetic acid; triethylamine; bis(tri-n-butyltin)oxide; dapsone; phenylboronic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0040-4039(95)02062-4

Reference yield:

: 174193-14-7
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-{2,4-dioxo-5-[3-(tetrahydro-pyran-2-yloxy)-prop-1-ynyl]-3,4-dihydro-2H-pyrimidin-1-yl}-tetrahydro-furan-3-yl ester

: 198822-78-5
Thiophosphoric acid O-{3-[1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propyl} ester S-phenyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: H₂

3: 99 percent / PhB(OH)2

4: 69 percent / H₂O / acetic acid

5: 84 percent / ClSiMe₃ / acetone / 20 h / Ambient temperature

6: 69 percent / DDS, 1H-tetrazole

7: (Bu₃Sn)2O / pyridine

8: TBAF / cyclohexane-d12

With 1H-tetrazole; chloro-trimethyl-silane; tetrabutyl ammonium fluoride; water; hydrogen; bis(tri-n-butyltin)oxide; dapsone; phenylboronic acid; In pyridine; Cyclohexane-d12; acetic acid; acetone;
DOI:10.1080/07328319708006125

Reference yield:

: 4105-38-8
Tri-O-acetyluridine

: 198822-78-5
Thiophosphoric acid O-{3-[1-((3aR,4R,6R,6aR)-6-hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-propyl} ester S-phenyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 94 percent / ICl / CH₂Cl₂ / 8 h / Heating

2: 80 percent / Pd(PPh₃)4, CuI, triethylamine / dimethylformamide / 20 h

3: H₂ / Pd/C / ethanol / 25 h

4: 0.5 M NaOH / pyridine / 0.17 h

5: 1.) PhB(OH)2; 2.) imidazole / 1.) pyridine, 1 h; 2.) DMF, 1.5 h

6: 69 percent / 80 percent AcOH / 12 h

7: 84 percent / TMSCl / acetone / 20 h

8: 69 percent / DDS, 1H-tetrazole / pyridine / 1 h

9: (Bu₃Sn)2O / pyridine / 1 h

10: TBAF*H₂O / tetrahydrofuran / 5 h

With 1H-imidazole; 1H-tetrazole; sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; chloro-trimethyl-silane; tetrabutyl ammonium fluoride; hydrogen; Iodine monochloride; acetic acid; triethylamine; bis(tri-n-butyltin)oxide; dapsone; phenylboronic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/0040-4039(95)02062-4