8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(dianilinophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine

Base Information

• Chemical Name: 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(dianilinophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine
• CAS No.: 239080-30-9
• Molecular Formula: C₃₄H₄₀BrN₆O₉P
• Molecular Weight: 787.604
• Mol file: 239080-30-9.mol

Synonyms:8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(dianilinophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine

Chemical Property of 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(dianilinophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(dianilinophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine

There total 15 articles about 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(dianilinophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine 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: 80.0%

8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(dianilinophosphoryl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine → 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(dianilinophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine (239080-30-9)

Guidance literature:

With acetic acid; at 20 ℃; for 3h;

DOI:10.1021/jo0000877

Reference yield: 80.0%

C54H56BrN6O10P (239080-29-6) → 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(dianilinophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine (239080-30-9)

Guidance literature:

With acetic acid; at 20 ℃;

DOI:10.1016/S0040-4039(99)00977-6

Reference yield:

5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine (239080-20-7) → 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(dianilinophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine (239080-30-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / K₂CO₃ / dimethylformamide / 2.5 h / 80 °C

2: 74 percent / dimethylformamide / 21 h / 50 °C

3: 87 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

4: 88 percent / N-bromoacetamide / tetrahydrofuran / 0.5 h / -10 °C

5: 98 percent / K₂CO₃ / dimethylformamide / 2.5 h / 50 °C

6: 90 percent / Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

7: 98 percent / tetrazole / pyridine / 47 h / 20 °C

8: 80 percent / aq. AcOH / 3 h / 20 °C

With 1H-imidazole; 1H-tetrazole; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; N-bromoacetamide; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; 1: Substitution / 2: Ring cleavage / 3: silylation / 4: Bromination / 5: Cyclization / 6: desilylation / 7: Substitution / 8: detritylation;

DOI:10.1021/jo0000877

upstream raw materials:

C₅₄H₅₆BrN₆O₁₀P

2',3'-O-isopropylideneinosine

5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

N-1-(2,4-dinitrophenyl)-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

Downstream raw materials:

C₄₆H₄₉BrN₆O₁₀P₂S₂