Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Base Information

• Chemical Name: Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
• CAS No.: 272116-47-9
• Molecular Formula: C₄₆H₅₃N₄O₈PS
• Molecular Weight: 852.989

Synonyms:Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Chemical Property of Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

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Technology Process of Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

There total 9 articles about Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-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: 95.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 5'-O-(4,4'-dimethoxytrityl)-5-(phenylthiomethyl)-2'-deoxyuridine (272116-56-0) → Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (272116-47-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.5h;

DOI:10.1021/ol005643y

Reference yield:

5-(phenylthiomethyl)-2'-deoxyuridine (272116-46-8) → Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (272116-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / 4-(dimethylamino)pyridine; pyridine; TEA / 3 h / 20 °C

2: diisopropylethylamine / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; dmap; TEA; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ja034866r

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2,4-dioxo-5-phenylsulfanylmethyl-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester (272116-47-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / 4-(dimethylamino)pyridine; pyridine; TEA / 3 h / 20 °C

2: diisopropylethylamine / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; dmap; TEA; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ja034866r

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

5'-O-(4,4'-dimethoxytrityl)-5-(phenylthiomethyl)-2'-deoxyuridine

2'-deoxyuridine

4,4'-dimethoxytrityl chloride

Downstream raw materials:

Diisopropyl-phosphoramidous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(2-oxo-5-phenylsulfanylmethyl-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

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