[(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid pentafluorophenyl ester

Base Information

• Chemical Name: [(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid pentafluorophenyl ester
• CAS No.: 221536-98-7
• Molecular Formula: C₄₀H₃₅F₅N₂O₉
• Molecular Weight: 782.718
• Mol file: 221536-98-7.mol

Synonyms:[(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid pentafluorophenyl ester

Chemical Property of [(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid pentafluorophenyl ester

There total 11 articles about [(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid pentafluorophenyl 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: 79.0%

pentafluorophenyl trifloroacetate (14533-84-7) + [(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid (221536-94-3) → [(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid pentafluorophenyl ester (221536-98-7)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(99)00147-1

Reference yield:

3-Benzyloxymethyl-1-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-5-methyl-1H-pyrimidine-2,4-dione → [(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid pentafluorophenyl ester (221536-98-7)

Guidance literature:

Multi-step reaction with 10 steps

1: NaH / dimethylformamide / 2 h / 0 °C

2: Bu₄NF / tetrahydrofuran / 3 h / 0 °C

3: 79 percent / DMAP, pyridine / 24 h / 50 °C

4: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 30 h / Ambient temperature

5: 70 percent / tetrahydrofuran / 14 h / 65 °C

6: 69 percent / conc.HCl(aq) / methanol / 36 h / 50 °C

7: 98 percent / H₂ / Pd-C (10 percent) / methanol / 24 h / 760 Torr / Ambient temperature

8: 95 percent / pyridine / CH₂Cl₂ / Ambient temperature

9: LiOH / methanol; H₂O / 6 h / Ambient temperature

10: 79 percent / pyridine / dimethylformamide / 1 h / Ambient temperature

With pyridine; hydrogenchloride; dmap; lithium hydroxide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)00147-1

Reference yield:

3-benzyloxymethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione (221536-67-0) → [(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid pentafluorophenyl ester (221536-98-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 30 h / Ambient temperature

2: 70 percent / tetrahydrofuran / 14 h / 65 °C

3: 69 percent / conc.HCl(aq) / methanol / 36 h / 50 °C

4: 98 percent / H₂ / Pd-C (10 percent) / methanol / 24 h / 760 Torr / Ambient temperature

5: 95 percent / pyridine / CH₂Cl₂ / Ambient temperature

6: LiOH / methanol; H₂O / 6 h / Ambient temperature

7: 79 percent / pyridine / dimethylformamide / 1 h / Ambient temperature

With pyridine; hydrogenchloride; lithium hydroxide; hydrogen; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)00147-1

upstream raw materials:

pentafluorophenyl trifloroacetate

[(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid

3-benzyloxymethyl-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methoxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

[(2S,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-acetic acid methyl ester