[(2S,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-phosphoramidic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester

Base Information

• Chemical Name: [(2S,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-phosphoramidic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester
• CAS No.: 146578-15-6
• Molecular Formula: C₄₉H₅₁N₈O₁₂P
• Molecular Weight: 974.964

Synonyms:

Chemical Property of [(2S,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-phosphoramidic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester

Chemical Property:

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Technology Process of [(2S,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-phosphoramidic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester

There total 6 articles about [(2S,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-phosphoramidic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl 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: 32.0%

C55H65N8O12PSi (146578-14-5,146610-84-6) → [(2S,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-phosphoramidic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester (146578-15-6,146610-85-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.75h;

DOI:10.1016/S0040-4039(00)60176-4

Reference yield:

Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl ester (146578-13-4) → [(2S,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-phosphoramidic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester (146578-15-6,146610-85-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / LiCl, pyridine / 16 h / Ambient temperature

2: 32 percent / tetrabutylammoniumfluoride / tetrahydrofuran / 0.75 h

With pyridine; tetrabutyl ammonium fluoride; lithium chloride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)60176-4

Reference yield:

5’-O-(4,4’dimethoxytrityl)-N6-(benzoyl)-3’-O-tert-butyldimethylsilyldeoxyadenosine (146578-12-3) → [(2S,3S,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-phosphoramidic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester (146578-15-6,146610-85-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / 80percent HOAc / 0.5 h / Ambient temperature

2: tetrazole / CH₂Cl₂; acetonitrile / 2 h / Ambient temperature

3: 79 percent / LiCl, pyridine / 16 h / Ambient temperature

4: 32 percent / tetrabutylammoniumfluoride / tetrahydrofuran / 0.75 h

With pyridine; 1H-tetrazole; tetrabutyl ammonium fluoride; acetic acid; lithium chloride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60176-4

upstream raw materials:

C₅₅H₆₅N₈O₁₂PSi

Phosphorous acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ylmethyl ester dimethyl ester

5’-O-(4,4’dimethoxytrityl)-N6-(benzoyl)-3’-O-tert-butyldimethylsilyldeoxyadenosine

6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine

Downstream raw materials:

C₅₈H₆₈N₁₀O₁₃P₂

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