(+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine

Base Information

• Chemical Name: (+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine
• CAS No.: 1307273-71-7
• Molecular Formula: C₃₆H₃₈FN₅O₈
• Molecular Weight: 687.725
• Mol file: 1307273-71-7.mol

Synonyms:(+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine

Chemical Property of (+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine

There total 10 articles about (+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine 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: 51.0%

(-)-[(1R,2R,3R,4S)-2-(benzoyloxy)-3-fluoro-4-hydroxy-5-methylenecyclopentyl]methyl benzoate (1307273-65-9) + N6,N6-bis(tert-butoxycarbonyl)adenine (309947-86-2) → (+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine (1307273-71-7)

Guidance literature:

N⁶,N⁶-bis(tert-butoxycarbonyl)adenine; With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 0.5h;

(-)-[(1R,2R,3R,4S)-2-(benzoyloxy)-3-fluoro-4-hydroxy-5-methylenecyclopentyl]methyl benzoate; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.bmcl.2011.08.113

Reference yield:

(-)-(3aR,4S,6R,6aR)-4-(benzyloxy)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenetetrahydro-3aH-cyclopenta[d][1,3]dioxole (1307273-59-1) → (+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine (1307273-71-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: trifluoroacetic acid / water / 3 h / 50 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

3.1: dimethylaminosulphur trifluoride / dichloromethane / 0.33 h / 20 °C

4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 20 °C

5.1: pyridine / 4 h / 20 °C

6.1: boron trichloride / dichloromethane / 0.75 h / -78 °C

7.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 0 °C

7.2: 3 h / 20 °C

With pyridine; 1H-imidazole; dimethylaminosulphur trifluoride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; boron trichloride; acetic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2011.08.113

Reference yield:

(3aS,4S,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenetetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-ol (1307273-58-0) → (+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine (1307273-71-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / water / 3 h / 50 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

4.1: dimethylaminosulphur trifluoride / dichloromethane / 0.33 h / 20 °C

5.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 20 °C

6.1: pyridine / 4 h / 20 °C

7.1: boron trichloride / dichloromethane / 0.75 h / -78 °C

8.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 0 °C

8.2: 3 h / 20 °C

With pyridine; 1H-imidazole; dimethylaminosulphur trifluoride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; boron trichloride; sodium hydride; acetic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.bmcl.2011.08.113

upstream raw materials:

(3aS,4S,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenetetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-ol

(-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate

(-)-[(1R,2R,3R,4S)-2-(benzoyloxy)-3-fluoro-4-hydroxy-5-methylenecyclopentyl]methyl benzoate

N⁶,N⁶-bis(tert-butoxycarbonyl)adenine

Downstream raw materials:

C₂₆H₂₂FN₅O₄