(+)-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
Hs Code.:

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

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

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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%

: 1307273-65-9
(-)-[(1R,2R,3R,4S)-2-(benzoyloxy)-3-fluoro-4-hydroxy-5-methylenecyclopentyl]methyl benzoate

: 309947-86-2
N⁶,N⁶-bis(tert-butoxycarbonyl)adenine

: 1307273-71-7
(+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine

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:

: 1307273-59-1
(-)-(3aR,4S,6R,6aR)-4-(benzyloxy)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenetetrahydro-3aH-cyclopenta[d][1,3]dioxole

: 1307273-71-7
(+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine

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:

: 1307273-58-0
(3aS,4S,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenetetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-ol

: 1307273-71-7
(+)-9-[(1R,2R,3R,4R)-2-fluoro-3-benzyloxy-4-(benzyloxymethyl)-5-methylenecyclopentan-1-yl]-6-N,N-di-Boc-adenine

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