(+)-1-{(1'R,2'S,3'R,4'R)-2',3'-Isopropylidenedioxy-4'-[(S)-benzyloxycarbonyl(benzyloxycarbonylamino)methyl]cyclopentyl}uracil

Base Information

• Chemical Name: (+)-1-{(1'R,2'S,3'R,4'R)-2',3'-Isopropylidenedioxy-4'-[(S)-benzyloxycarbonyl(benzyloxycarbonylamino)methyl]cyclopentyl}uracil
• CAS No.: 196397-51-0
• Molecular Formula: C₂₉H₃₁N₃O₈
• Molecular Weight: 549.58
• Mol file: 196397-51-0.mol

Synonyms:(+)-1-{(1'R,2'S,3'R,4'R)-2',3'-Isopropylidenedioxy-4'-[(S)-benzyloxycarbonyl(benzyloxycarbonylamino)methyl]cyclopentyl}uracil

Chemical Property of (+)-1-{(1'R,2'S,3'R,4'R)-2',3'-Isopropylidenedioxy-4'-[(S)-benzyloxycarbonyl(benzyloxycarbonylamino)methyl]cyclopentyl}uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-1-{(1'R,2'S,3'R,4'R)-2',3'-Isopropylidenedioxy-4'-[(S)-benzyloxycarbonyl(benzyloxycarbonylamino)methyl]cyclopentyl}uracil

There total 13 articles about (+)-1-{(1'R,2'S,3'R,4'R)-2',3'-Isopropylidenedioxy-4'-[(S)-benzyloxycarbonyl(benzyloxycarbonylamino)methyl]cyclopentyl}uracil 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: 86.0%

2,2-dimethoxy-propane (77-76-9) + (S)-Benzyloxycarbonylamino-[(1R,2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,3-dihydroxy-cyclopentyl]-acetic acid benzyl ester (174742-33-7) → (+)-1-{(1'R,2'S,3'R,4'R)-2',3'-Isopropylidenedioxy-4'-[(S)-benzyloxycarbonyl(benzyloxycarbonylamino)methyl]cyclopentyl}uracil (196397-51-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 1h; Ambient temperature;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (+)-1-{(1'R,2'S,3'R,4'R)-2',3'-Isopropylidenedioxy-4'-[(S)-benzyloxycarbonyl(benzyloxycarbonylamino)methyl]cyclopentyl}uracil (196397-51-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / aq. NaHCO₃ / tetrahydrofuran / 1 h / 0 - 20 °C

2: 1.) HMDS, TMSCl / 2.) Pd(PPh₃)4 / 1.) CH₃CN, r.t., 30 min, 2.) CH₃CN, r.t., 24 h

3: NaHCO₃ / dimethylformamide / 24 h / Ambient temperature

4: tetrahydrofuran / 15 h / Ambient temperature; OsO₄; also other oxidant; different solvents and reagents

5: 86 percent / p-TsOH*H₂O / acetone / 1 h / Ambient temperature

With chloro-trimethyl-silane; sodium hydrogencarbonate; toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

Reference yield:

(3S,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (151765-22-9) → (+)-1-{(1'R,2'S,3'R,4'R)-2',3'-Isopropylidenedioxy-4'-[(S)-benzyloxycarbonyl(benzyloxycarbonylamino)methyl]cyclopentyl}uracil (196397-51-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 60 percent / Ph₃P, ZnBr₂, DEAD / tetrahydrofuran / 0.5 h / Ambient temperature

2: 87 percent / NaN₃ / dimethylsulfoxide / 24 h / Ambient temperature

3: 92 percent / Ph₃P, H₂O / tetrahydrofuran / 24 h / Ambient temperature

4: 94 percent / aq. NaHCO₃ / tetrahydrofuran / 1 h / 0 - 20 °C

5: 1.) HMDS, TMSCl / 2.) Pd(PPh₃)4 / 1.) CH₃CN, r.t., 30 min, 2.) CH₃CN, r.t., 24 h

6: NaHCO₃ / dimethylformamide / 24 h / Ambient temperature

7: tetrahydrofuran / 15 h / Ambient temperature; OsO₄; also other oxidant; different solvents and reagents

8: 86 percent / p-TsOH*H₂O / acetone / 1 h / Ambient temperature

With chloro-trimethyl-silane; sodium azide; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; zinc dibromide; diethylazodicarboxylate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

upstream raw materials:

2,2-dimethoxy-propane

(S)-Benzyloxycarbonylamino-[(1R,2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,3-dihydroxy-cyclopentyl]-acetic acid benzyl ester

benzyl chloroformate

(3S,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

(S)-Benzyloxycarbonylamino-[(1R,2R,3S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,3-dihydroxy-cyclopentyl]-acetic acid benzyl ester