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

Base Information

Chemical Name:8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(bisphenylthiophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine
CAS No.:295805-80-0
Molecular Formula:C₃₄H₃₈BrN₄O₉PS₂
Molecular Weight:821.707
Hs Code.:

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

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

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

There total 8 articles about 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(bisphenylthiophosphoryl)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: 87.0%

: 295805-79-7
8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(bisphenylthiophosphoryl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

: 295805-80-0
8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(bisphenylthiophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine

Guidance literature:: With acetic acid; at 20 ℃;
DOI:10.1021/jo0000877

Reference yield:

: 2140-11-6
2',3'-O-isopropylideneinosine

: 295805-80-0
8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(bisphenylthiophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine

Guidance literature:: Multi-step reaction with 9 steps

1: 100 percent / pyridine / 40 h / 20 °C

2: 90 percent / K₂CO₃ / dimethylformamide / 2.5 h / 80 °C

3: 74 percent / dimethylformamide / 21 h / 50 °C

4: 87 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

5: 88 percent / N-bromoacetamide / tetrahydrofuran / 0.5 h / -10 °C

6: 98 percent / K₂CO₃ / dimethylformamide / 2.5 h / 50 °C

7: 90 percent / Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

8: 75 percent / tetrazole; 2,4,6-triisopropylbenzenesulfonyl chloride / pyridine / 20 °C

9: 87 percent / aq. AcOH / 20 °C

With 1H-imidazole; 1H-tetrazole; 2,4,6-triisopropylphenylsulfonyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; N-bromoacetamide; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; 1: Alkylation / 2: Substitution / 3: Ring cleavage / 4: silylation / 5: Bromination / 6: Cyclization / 7: desilylation / 8: Substitution / 9: detritylation;
DOI:10.1021/jo0000877

Reference yield:

: 239080-21-8
N-1-(2,4-dinitrophenyl)-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

: 295805-80-0
8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(bisphenylthiophosphoryl)oxy]methyl]cyclopentyl]-2',3'-O-isopropylideneinosine

Guidance literature:: Multi-step reaction with 7 steps

1: 74 percent / dimethylformamide / 21 h / 50 °C

2: 87 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

3: 88 percent / N-bromoacetamide / tetrahydrofuran / 0.5 h / -10 °C

4: 98 percent / K₂CO₃ / dimethylformamide / 2.5 h / 50 °C

5: 90 percent / Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

6: 75 percent / tetrazole; 2,4,6-triisopropylbenzenesulfonyl chloride / pyridine / 20 °C

7: 87 percent / aq. AcOH / 20 °C

With 1H-imidazole; 1H-tetrazole; 2,4,6-triisopropylphenylsulfonyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; N-bromoacetamide; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; 1: Ring cleavage / 2: silylation / 3: Bromination / 4: Cyclization / 5: desilylation / 6: Substitution / 7: detritylation;
DOI:10.1021/jo0000877