9-[(3aS,4R,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6-a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-ylamine

Base Information

Chemical Name:9-[(3aS,4R,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6-a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-ylamine
CAS No.:474329-20-9
Molecular Formula:C₃₃H₃₁N₅O₃
Molecular Weight:545.641
Hs Code.:

Synonyms:9-[(3aS,4R,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6-a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-ylamine

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Chemical Property of 9-[(3aS,4R,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6-a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-ylamine

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Technology Process of 9-[(3aS,4R,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6-a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-ylamine

There total 8 articles about 9-[(3aS,4R,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6-a-dihydro-3aH-cyclopenta[1,3]dioxol-4-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%

: 73-24-5,71660-29-2,71660-30-5
7H-purin-6-ylamine

: 474329-19-6
methanesulfonic acid (3aS,4S,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester

: 7-[(3aS,4R,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-7H-purin-6-ylamine

: 474329-20-9
9-[(3aS,4R,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6-a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-ylamine

Guidance literature:: With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 12h;
DOI:10.1021/ol026624m

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 474329-20-9
9-[(3aS,4R,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6-a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-ylamine

Guidance literature:: Multi-step reaction with 8 steps

1: 81 percent / tetrahydrofuran / 3 h / 0 °C

2: 85 percent / NaIO₄ / CH₂Cl₂ / 0.5 h / 20 °C

3: 95 percent / K₂CO₃ / H₂O; methanol / 36 h / pH 10 / Heating

4: 81 percent / potassium tert-butoxide / tetrahydrofuran / 15 h / 20 °C

5: 99 percent / second-generation Grubbs catalyst / CH₂Cl₂ / 2 h / 20 °C

6: 78 percent / 4-(dimethylamino)pyridine; pyridine / 20 h / 20 °C

7: 72 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

8: NH₃ / methanol / 80 °C

With pyridine; dmap; sodium periodate; potassium tert-butylate; ammonia; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo0503207

Reference yield:

: 141436-58-0,126113-84-6
(-)-(1R)-1-[(4R,5S)-5-((1S)-1-hydroxyallyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol

: 474329-20-9
9-[(3aS,4R,6aS)-2,2-dimethyl-6a-trityloxymethyl-4,6-a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-ylamine

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / NaIO₄ / CH₂Cl₂ / 0.5 h / 20 °C

2: 95 percent / K₂CO₃ / H₂O; methanol / 36 h / pH 10 / Heating

3: 81 percent / potassium tert-butoxide / tetrahydrofuran / 15 h / 20 °C

4: 99 percent / second-generation Grubbs catalyst / CH₂Cl₂ / 2 h / 20 °C

5: 78 percent / 4-(dimethylamino)pyridine; pyridine / 20 h / 20 °C

6: 72 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

7: NH₃ / methanol / 80 °C

With pyridine; dmap; sodium periodate; potassium tert-butylate; ammonia; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/jo0503207