Methanesulfonic acid 2-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-tetrahydro-furan-2-yl}-ethyl ester

Base Information

• Chemical Name: Methanesulfonic acid 2-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-tetrahydro-furan-2-yl}-ethyl ester
• CAS No.: 1026348-82-2
• Molecular Formula: C₄₀H₄₁N₃O₈S₂
• Molecular Weight: 755.913

Synonyms:

Chemical Property of Methanesulfonic acid 2-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-tetrahydro-furan-2-yl}-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid 2-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-tetrahydro-furan-2-yl}-ethyl ester

There total 12 articles about Methanesulfonic acid 2-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-tetrahydro-furan-2-yl}-ethyl 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:

Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester (441044-21-9) → Methanesulfonic acid 2-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-tetrahydro-furan-2-yl}-ethyl ester (1026348-82-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: imidazole; acetic acid / dimethylformamide / 0.83 h

2.1: NaOH / methanol; H₂O

3.1: 21.90 g / 4-dimethylaminopyridine; triethylamine / tetrahydrofuran; methanol / 1.17 h

4.1: N-methyl-N-trimethylsilyltrifluoroacetamide / acetonitrile / 0.5 h

4.2: SnCl₄ / acetonitrile / 0.5 h / 20 °C

5.1: 5.432 g / NaOH / H₂O; methanol / 0.01 h / 20 °C

6.1: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / -20 - 20 °C

7.1: 83 percent Spectr_. / dimethylformamide / 1.5 h / 20 °C

8.1: 86 percent / Bu₃SnH; azobisisobutyronitrile / toluene / 0.03 h / Heating

9.1: NaOH; water

10.1: triethylamine / tetrahydrofuran

11.1: Bu₄N⁽¹⁺⁾*F^(1-) / H₂O

12.1: triethylamine / tetrahydrofuran

With 1H-imidazole; dmap; sodium hydroxide; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: Vorbrueggen reaction / 6.1: Mitsunobu reaction / 8.1: Barton deoxygenation;

DOI:10.1021/jo0003910

Reference yield:

Benzoic acid (2R,3S,4R)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-5-methoxy-tetrahydro-furan-3-ylmethyl ester → Methanesulfonic acid 2-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-tetrahydro-furan-2-yl}-ethyl ester (1026348-82-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaOH / methanol; H₂O

2.1: 21.90 g / 4-dimethylaminopyridine; triethylamine / tetrahydrofuran; methanol / 1.17 h

3.1: N-methyl-N-trimethylsilyltrifluoroacetamide / acetonitrile / 0.5 h

3.2: SnCl₄ / acetonitrile / 0.5 h / 20 °C

4.1: 5.432 g / NaOH / H₂O; methanol / 0.01 h / 20 °C

5.1: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / -20 - 20 °C

6.1: 83 percent Spectr_. / dimethylformamide / 1.5 h / 20 °C

7.1: 86 percent / Bu₃SnH; azobisisobutyronitrile / toluene / 0.03 h / Heating

8.1: NaOH; water

9.1: triethylamine / tetrahydrofuran

10.1: Bu₄N⁽¹⁺⁾*F^(1-) / H₂O

11.1: triethylamine / tetrahydrofuran

With dmap; sodium hydroxide; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Vorbrueggen reaction / 5.1: Mitsunobu reaction / 7.1: Barton deoxygenation;

DOI:10.1021/jo0003910

Reference yield:

N4-benzoyl-1-[(2R,3R,4R,5R)-5-(2-tertbutyldiphenylsilyloxyethyl)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl]cytosine (208463-23-4) → Methanesulfonic acid 2-{(2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-[bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-tetrahydro-furan-2-yl}-ethyl ester (1026348-82-2)

Guidance literature:

Multi-step reaction with 7 steps

1: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / -20 - 20 °C

2: 83 percent Spectr_. / dimethylformamide / 1.5 h / 20 °C

3: 86 percent / Bu₃SnH; azobisisobutyronitrile / toluene / 0.03 h / Heating

4: NaOH; water

5: triethylamine / tetrahydrofuran

6: Bu₄N⁽¹⁺⁾*F^(1-) / H₂O

7: triethylamine / tetrahydrofuran

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; water; tri-n-butyl-tin hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene; 1: Mitsunobu reaction / 3: Barton deoxygenation;

DOI:10.1021/jo0003910

upstream raw materials:

methanesulfonyl chloride

N-{1-[(2R,4S,5R)-4-[Bis-(4-methoxy-phenyl)-phenyl-methylsulfanylmethyl]-5-(2-hydroxy-ethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

Benzoic acid (2R,3S,4R)-4-hydroxy-2-(2-hydroxy-ethyl)-5-methoxy-tetrahydro-furan-3-ylmethyl ester

N⁴-benzoyl-1-[(2R,3R,4R,5R)-5-(2-tertbutyldiphenylsilyloxyethyl)-3-hydroxy-4-hydroxymethyltetrahydrofuran-2-yl]cytosine

Downstream raw materials:

C₅₁H₅₅N₅O₁₁S₃

C₇₁H₇₁N₅O₁₁S₂

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