{9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester

Base Information

• Chemical Name: {9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester
• CAS No.: 116597-20-7
• Molecular Formula: C₅₂H₅₁N₅O₁₁
• Molecular Weight: 922.004

Synonyms:

Chemical Property of {9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester

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Technology Process of {9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester

There total 7 articles about {9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid 9H-fluoren-9-ylmethyl 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: 75.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N2-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine (116597-19-4) → {9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester (116597-20-7)

Guidance literature:

With pyridine; dmap; Ambient temperature;

DOI:10.1021/jo00256a025

Reference yield:

4-methoxy-2,6-dihydropyran (17327-22-9) → {9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester (116597-20-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / mesitylenesulfonic acid / tetrahydrofuran / 15 h / 0 °C

2: 69 percent / tetrabutylammonium fluoride / tetrahydrofuran; H₂O; pyridine / 3 h / 0 °C

3: 75 percent / pyridine, 4-(dimethylamino)pyridine / Ambient temperature

With pyridine; dmap; mesitylene sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; water;

DOI:10.1021/jo00256a025

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) → {9-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-carbamic acid 9H-fluoren-9-ylmethyl ester (116597-20-7)

Guidance literature:

Multi-step reaction with 5 steps

2: 68 percent / pyridine / 4 h

3: 90 percent / mesitylenesulfonic acid / tetrahydrofuran / 15 h / 0 °C

4: 69 percent / tetrabutylammonium fluoride / tetrahydrofuran; H₂O; pyridine / 3 h / 0 °C

5: 75 percent / pyridine, 4-(dimethylamino)pyridine / Ambient temperature

With pyridine; dmap; mesitylene sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; water;

DOI:10.1021/jo00256a025

upstream raw materials:

4,4'-dimethoxytrityl chloride

N²-<<(9-fluorenylmethyl)oxy>carbonyl>-2'-O-(4-methoxytetrahydropyran-4-yl)guanosine

4-methoxy-2,6-dihydropyran

(fluorenylmethoxy)carbonyl chloride

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