(3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine

Base Information

• Chemical Name: (3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine
• CAS No.: 142941-43-3
• Molecular Formula: C₁₇H₁₉N₅O₂
• Molecular Weight: 325.37
• Mol file: 142941-43-3.mol

Synonyms:(3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine

Chemical Property of (3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine

There total 10 articles about (3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine 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: 46.0%

(2R,4S)-2-<(benzyloxy)methyl>-4-<(methylsulfonyl)oxy>tetrahydrofuran (142941-41-1) + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → (3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine (142941-43-3)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 85 ℃; for 18h;

Reference yield:

3-deoxy-1,2:5,6-di-O-isopropylidene-β-D-lyxo-hexose (32785-98-1) → (3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine (142941-43-3)

Guidance literature:

Multi-step reaction with 8 steps

1: HCl / methanol; H₂O

2: NaIO₄ / methanol; H₂O / 0.25 h

3: NaBH₄ / methanol / 0.42 h

4: 1) NaH, 2) Bu₄NI / 1) THF, 20 min, 2) THF, 50 deg C, 1.5 h

5: 94 percent / Dowex 50W-X₈(H) resin / 18 h / Heating

6: 87 percent / Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 44 h / Ambient temperature

7: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h

8: 46 percent / K₂CO₃ / dimethylsulfoxide / 18 h / 85 °C

With hydrogenchloride; triethylsilane; dmap; sodium tetrahydroborate; sodium periodate; Dowex 50W-X₈(H) resin; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; In methanol; dichloromethane; water; dimethyl sulfoxide;

Reference yield:

3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol (78038-33-2) → (3'R,5'R)-9-<5'-<(benzyloxy)methyl>tetrahydrofuran-3'-yl>9H-purin-6-amine (142941-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h

2: 46 percent / K₂CO₃ / dimethylsulfoxide / 18 h / 85 °C

With dmap; potassium carbonate; In dichloromethane; dimethyl sulfoxide;

upstream raw materials:

(2R,4S)-2-<(benzyloxy)methyl>-4-<(methylsulfonyl)oxy>tetrahydrofuran

adenine

3-deoxy-1,2:5,6-di-O-isopropylidene-β-D-lyxo-hexose

3S,5R-5-<(benzyloxy)methyl>tetrahydrofuran-3-ol

Downstream raw materials:

IsoddA