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

Base Information

• Chemical Name: S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine-3'-phosphorodithioate
• CAS No.: 90762-77-9
• Molecular Formula: C₆₄H₆₁N₆O₁₁PS₂
• Molecular Weight: 1185.33

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

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

Chemical Property:

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

There total 10 articles about S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O⁶-(diphenylcarbamoyl)-N²-propionylguanosine-3'-phosphorodithioate 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: 91.0%

cyclohexylammonium S,S-diphenyl phosphorodithioate + 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O6-(diphenylcarbamoyl)-N2-propionylguanosine (90742-19-1) → S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O6-(diphenylcarbamoyl)-N2-propionylguanosine-3'-phosphorodithioate (90762-77-9)

Guidance literature:

With pyridine; for 5.5h;

DOI:10.1021/ja00328a042

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O6-(diphenylcarbamoyl)-N2-propionylguanosine-3'-phosphorodithioate (90762-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1: TFA / CH₂Cl₂ / 11 h

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

3: 94 percent / pyridine / 0.5 h

4: 91 percent / pyridine, MDS / 5.5 h

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

DOI:10.1021/ja00328a042

Reference yield:

2',3',5'-tri-O-propionyl-N2-propionylguanosine (90742-12-4) → S,S-diphenyl 2'-O-(tetrahydropyran-2-yl)-5'-O-(4,4'-dimethoxytrityl)-O6-(diphenylcarbamoyl)-N2-propionylguanosine-3'-phosphorodithioate (90762-77-9)

Guidance literature:

Multi-step reaction with 7 steps

1: i-Pr₂NEt / pyridine / 1 h / Ambient temperature

2: 2M NaOH / pyridine; ethanol / 0 °C

3: 90 percent / pyridine / 2 h

4: TFA / CH₂Cl₂ / 11 h

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

6: 94 percent / pyridine / 0.5 h

7: 91 percent / pyridine, MDS / 5.5 h

With pyridine; potassium fluoride; sodium hydroxide; tetraethylammonium bromide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In pyridine; ethanol; dichloromethane; acetonitrile;

DOI:10.1021/ja00328a042

upstream raw materials:

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

3,4-dihydro-2H-pyran

4,4'-dimethoxytrityl chloride

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

Downstream raw materials:

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

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

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