Phosphoric acid mono-[(2R,3S,5R)-3-[2-(4-hydroxy-phenyl)-2-oxo-ethylsulfanyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester

Base Information

• Chemical Name: Phosphoric acid mono-[(2R,3S,5R)-3-[2-(4-hydroxy-phenyl)-2-oxo-ethylsulfanyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester
• CAS No.: 502635-64-5
• Molecular Formula: C₁₈H₂₁N₂O₉PS
• Molecular Weight: 472.413

Synonyms:Phosphoric acid mono-[(2R,3S,5R)-3-[2-(4-hydroxy-phenyl)-2-oxo-ethylsulfanyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester

Chemical Property of Phosphoric acid mono-[(2R,3S,5R)-3-[2-(4-hydroxy-phenyl)-2-oxo-ethylsulfanyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester

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Technology Process of Phosphoric acid mono-[(2R,3S,5R)-3-[2-(4-hydroxy-phenyl)-2-oxo-ethylsulfanyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester

There total 6 articles about Phosphoric acid mono-[(2R,3S,5R)-3-[2-(4-hydroxy-phenyl)-2-oxo-ethylsulfanyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] 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: 90.0%

p-hydroxyphenacyl bromide + 3'-thio-2'-deoxythymidine phosphate (502635-63-4) → Phosphoric acid mono-[(2R,3S,5R)-3-[2-(4-hydroxy-phenyl)-2-oxo-ethylsulfanyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester (502635-64-5)

Guidance literature:

With HEPES buffer; In ethanol; water; at 20 ℃; for 2h; pH=7.0;

DOI:10.1016/S0040-4039(02)02194-9

Reference yield:

5'-O-monomethoxytrityl-3'-S-benzoyl-3'-thiothymidine (119038-34-5) → Phosphoric acid mono-[(2R,3S,5R)-3-[2-(4-hydroxy-phenyl)-2-oxo-ethylsulfanyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester (502635-64-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / AcOH / 24 h / 20 °C

2: 58 percent / POCl₃; trimethylphosphate / 22 h / 0 °C

3: 88 percent / NaOH / ethanol / 1.17 h / 0 °C

4: 90 percent / HEPES buffer / ethanol; H₂O / 2 h / 20 °C / pH 7.0

With trimethyl phosphite; sodium hydroxide; HEPES buffer; acetic acid; trichlorophosphate; In ethanol; water;

DOI:10.1016/S0040-4039(02)02194-9

Reference yield:

(2R,4R,5R)-1-[5-[bis(4-methoxyphenyl)phenylmethoxymethyl]-4-hydroxytetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (124680-51-9) → Phosphoric acid mono-[(2R,3S,5R)-3-[2-(4-hydroxy-phenyl)-2-oxo-ethylsulfanyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl] ester (502635-64-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / pyridine / 22 h / 0 °C

2: 55 percent / dimethylformamide / 22 h / 100 °C

3: 85 percent / AcOH / 24 h / 20 °C

4: 58 percent / POCl₃; trimethylphosphate / 22 h / 0 °C

5: 88 percent / NaOH / ethanol / 1.17 h / 0 °C

6: 90 percent / HEPES buffer / ethanol; H₂O / 2 h / 20 °C / pH 7.0

With pyridine; trimethyl phosphite; sodium hydroxide; HEPES buffer; acetic acid; trichlorophosphate; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(02)02194-9

upstream raw materials:

3'-thio-2'-deoxythymidine phosphate

5'-O-monomethoxytrityl-3'-S-benzoyl-3'-thiothymidine

(2R,4R,5R)-1-[5-[bis(4-methoxyphenyl)phenylmethoxymethyl]-4-hydroxytetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

3'-S-benzoyl-3'-thiothymidine

Downstream raw materials:

4-hydroxyphenylacetate

4-Hydroxyacetophenone

3'-thio-2'-deoxythymidine phosphate

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