9-[(2R,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-yl]-9H-purin-6-ylamine

Base Information

Chemical Name:9-[(2R,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-yl]-9H-purin-6-ylamine
CAS No.:250696-92-5
Molecular Formula:C₁₈H₂₁N₅O₂
Molecular Weight:339.397
Hs Code.:

Synonyms:9-[(2R,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-yl]-9H-purin-6-ylamine

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Chemical Property of 9-[(2R,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-yl]-9H-purin-6-ylamine

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Technology Process of 9-[(2R,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-yl]-9H-purin-6-ylamine

There total 13 articles about 9-[(2R,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-yl]-9H-purin-6-ylamine 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: 61.0%

: 66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9
adenine

: 250696-91-4
6-O-benzyl-3-O-mesyl-1,2,5-trideoxy-D-allofuranose

: 250696-92-5
9-[(2R,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-yl]-9H-purin-6-ylamine

Guidance literature:: With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃;
DOI:10.1080/07328319908044857

Reference yield:

: 29474-73-5
(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate

: 250696-92-5
9-[(2R,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-yl]-9H-purin-6-ylamine

Guidance literature:: Multi-step reaction with 12 steps

1: 76 percent / 0.4 percent HCl / acetonitrile; H₂O / 8 h / 20 °C

2: 92 percent / imidazole / dimethylformamide; CH₂Cl₂ / -15 - 0 °C

3: 89 percent / 1,2-dichloro-ethane / 4 h / Heating

4: 87 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

5: 78 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

6: 6.07 g / NaH / tetrahydrofuran / 20 °C

7: 64 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / -15 - 20 °C

8: 82 percent / 1,2-dichloro-ethane / 3 h / Heating

9: 88 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

10: 90 percent / CH₃ONa / methanol / 6 h / 20 °C

11: 83 percent / Et₃N / CH₂Cl₂ / 6 h / 0 °C

12: 61 percent / K₂CO₃; 18-crown-6 / dimethylformamide / 50 °C

With 1H-imidazole; hydrogenchloride; triethylsilane; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Hydrolysis / 2: Silylation / 3: Esterification / 4: Reduction / 5: Desilylation / 6: Benzylation / 7: Reductive cleavage / 8: Esterification / 9: Reduction / 10: Deacylation / 11: Mesylation / 12: Coupling;
DOI:10.1080/07328319908044857

Reference yield:

: 31795-13-8
3-O-benzoyl-1,2-O-isopropylidene-α-D-allofuranose

: 250696-92-5
9-[(2R,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-furan-3-yl]-9H-purin-6-ylamine

Guidance literature:: Multi-step reaction with 11 steps

1: 92 percent / imidazole / dimethylformamide; CH₂Cl₂ / -15 - 0 °C

2: 89 percent / 1,2-dichloro-ethane / 4 h / Heating

3: 87 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

4: 78 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

5: 6.07 g / NaH / tetrahydrofuran / 20 °C

6: 64 percent / TMSOTf; Et₃SiH / CH₂Cl₂ / -15 - 20 °C

7: 82 percent / 1,2-dichloro-ethane / 3 h / Heating

8: 88 percent / n-Bu₃SnH; AIBN / toluene / 3 h / Heating

9: 90 percent / CH₃ONa / methanol / 6 h / 20 °C

10: 83 percent / Et₃N / CH₂Cl₂ / 6 h / 0 °C

11: 61 percent / K₂CO₃; 18-crown-6 / dimethylformamide / 50 °C

With 1H-imidazole; triethylsilane; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 1: Silylation / 2: Esterification / 3: Reduction / 4: Desilylation / 5: Benzylation / 6: Reductive cleavage / 7: Esterification / 8: Reduction / 9: Deacylation / 10: Mesylation / 11: Coupling;
DOI:10.1080/07328319908044857