Phosphoric acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenylsulfanyl)-phosphoryloxymethyl]-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-5-[6-oxo-2-(trityl-amino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: Phosphoric acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenylsulfanyl)-phosphoryloxymethyl]-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-5-[6-oxo-2-(trityl-amino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2,2,2-trichloro-ethyl ester
• CAS No.: 83919-70-4
• Molecular Formula: C₅₁H₅₂Cl₃N₅O₁₃P₂S₂
• Molecular Weight: 1175.44

Synonyms:

Chemical Property of Phosphoric acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenylsulfanyl)-phosphoryloxymethyl]-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-5-[6-oxo-2-(trityl-amino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2,2,2-trichloro-ethyl ester

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Technology Process of Phosphoric acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenylsulfanyl)-phosphoryloxymethyl]-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-5-[6-oxo-2-(trityl-amino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2,2,2-trichloro-ethyl ester

There total 8 articles about Phosphoric acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenylsulfanyl)-phosphoryloxymethyl]-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-5-[6-oxo-2-(trityl-amino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2,2,2-trichloro-ethyl ester 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:

3',5'-di-O-acetyl-N2-benzoylguanosine (66781-55-3) → Phosphoric acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenylsulfanyl)-phosphoryloxymethyl]-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-5-[6-oxo-2-(trityl-amino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2,2,2-trichloro-ethyl ester (83919-70-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / p-TsOH / dioxane / 3 h

2: 76 percent / butylamine / methanol / 24 h / Ambient temperature

3: 90 percent / pyridine / 2 h / 60 °C

4: pyridine / 6 h / 80 °C

5: 90 percent / butylamine / methanol / 24 h / Ambient temperature

6: 74 percent / TPS, pyridine / 3 h

7: TPS, pyridine / 24 h / Ambient temperature

With pyridine; toluene-4-sulfonic acid; N-butylamine; In 1,4-dioxane; methanol;

DOI:10.1246/bcsj.55.2949

Reference yield:

4-methoxy-2,6-dihydropyran (17327-22-9) → Phosphoric acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenylsulfanyl)-phosphoryloxymethyl]-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-5-[6-oxo-2-(trityl-amino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2,2,2-trichloro-ethyl ester (83919-70-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 71 percent / p-TsOH / dioxane / 3 h

2: 76 percent / butylamine / methanol / 24 h / Ambient temperature

3: 90 percent / pyridine / 2 h / 60 °C

4: pyridine / 6 h / 80 °C

5: 90 percent / butylamine / methanol / 24 h / Ambient temperature

6: 74 percent / TPS, pyridine / 3 h

7: TPS, pyridine / 24 h / Ambient temperature

With pyridine; toluene-4-sulfonic acid; N-butylamine; In 1,4-dioxane; methanol;

DOI:10.1246/bcsj.55.2949

Reference yield:

2'-O-(4-methoxytetrahydropyran-4-yl)guanosine (69471-61-0) → Phosphoric acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenylsulfanyl)-phosphoryloxymethyl]-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-5-[6-oxo-2-(trityl-amino)-1,6-dihydro-purin-9-yl]-tetrahydro-furan-3-yl ester 2,2,2-trichloro-ethyl ester (83919-70-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridine / 2 h / 60 °C

2: pyridine / 6 h / 80 °C

3: 90 percent / butylamine / methanol / 24 h / Ambient temperature

4: 74 percent / TPS, pyridine / 3 h

5: TPS, pyridine / 24 h / Ambient temperature

With pyridine; N-butylamine; In methanol;

DOI:10.1246/bcsj.55.2949

upstream raw materials:

2,2,2-trichloroethyl dihydrogen phosphate

S,S-bis(4-methoxyphenyl)-2'-O-(4-methoxytetrahydropyran-4-yl)-N²-tritylguanosine-5'-phosphorodithioate

3',5'-di-O-acetyl-N²-benzoylguanosine

4-methoxy-2,6-dihydropyran

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