2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine

Base Information

• Chemical Name: 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine
• CAS No.: 90742-19-1
• Molecular Formula: C₅₂H₅₂N₆O₁₀
• Molecular Weight: 921.019

Synonyms:2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine

Chemical Property of 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine

There total 8 articles about 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine 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: 94.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O-(tetrahydropyran-2-yl)-O6-(diphenylcarbamoyl)-N2-propionylguanosine (90742-18-0) → 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O6-(diphenylcarbamoyl)-N2-propionylguanosine (90742-19-1)

Guidance literature:

With pyridine; for 0.5h;

DOI:10.1021/ja00328a042

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O6-(diphenylcarbamoyl)-N2-propionylguanosine (90742-19-1)

Guidance literature:

Multi-step reaction with 3 steps

1: TFA / CH₂Cl₂ / 11 h

2: KF, Et₄NBr H₂O / acetonitrile / 0.75 h / 50 °C

3: 94 percent / pyridine / 0.5 h

With pyridine; potassium fluoride; tetraethylammonium bromide; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1021/ja00328a042

Reference yield:

Propionic acid (2R,3R,4R,5R)-2-(6-diphenylcarbamoyloxy-2-propionylamino-purin-9-yl)-4-propionyloxy-5-propionyloxymethyl-tetrahydro-furan-3-yl ester (98264-10-9) → 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O6-(diphenylcarbamoyl)-N2-propionylguanosine (90742-19-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 2M NaOH / pyridine; ethanol / 0 °C

2: 90 percent / pyridine / 2 h

3: TFA / CH₂Cl₂ / 11 h

4: KF, Et₄NBr H₂O / acetonitrile / 0.75 h / 50 °C

5: 94 percent / pyridine / 0.5 h

With pyridine; potassium fluoride; sodium hydroxide; tetraethylammonium bromide; trifluoroacetic acid; In pyridine; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/ja00328a042

upstream raw materials:

4,4'-dimethoxytrityl chloride

2'-O-(tetrahydropyran-2-yl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine

3,4-dihydro-2H-pyran

2',3',5'-tri-O-propionyl-N²-propionylguanosine

Downstream raw materials:

S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine-3'-phosphorodithioate

Diphenyl-carbamic acid 9-[(2R,3R,4R,5R)-4-(bis-phenylsulfanyl-phosphoryloxy)-5-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-2-propionylamino-9H-purin-6-yl ester

Diphenyl-carbamic acid 9-[(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(hydroxy-phenylsulfanyl-phosphoryloxy)-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-2-propionylamino-9H-purin-6-yl ester

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