(2R,3S,5R)-2-({1-[(2S,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl]}-1H-1,2,3-triazol-4-yl)-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite

Base Information

• Chemical Name: (2R,3S,5R)-2-({1-[(2S,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl]}-1H-1,2,3-triazol-4-yl)-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite
• CAS No.: 1262311-78-3
• Molecular Formula: C₅₁H₆₀N₉O₁₁P
• Molecular Weight: 1006.06

Synonyms:(2R,3S,5R)-2-({1-[(2S,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl]}-1H-1,2,3-triazol-4-yl)-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite

Chemical Property of (2R,3S,5R)-2-({1-[(2S,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl]}-1H-1,2,3-triazol-4-yl)-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite

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Technology Process of (2R,3S,5R)-2-({1-[(2S,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl]}-1H-1,2,3-triazol-4-yl)-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite

There total 7 articles about (2R,3S,5R)-2-({1-[(2S,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl]}-1H-1,2,3-triazol-4-yl)-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite 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: 65.0%

1-[(2R,4S,5S)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-(4-{(2R,3S,5R)-3-hydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-2-yl}-1H-1,2,3-triazol-1-yl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (1262311-81-8) + β-cyanoethoxy-N,N,N',N'-tetramethylphosphorodiamidite (196958-10-8) → (2R,3S,5R)-2-({1-[(2S,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl]}-1H-1,2,3-triazol-4-yl)-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite (1262311-78-3)

Guidance literature:

1-[(2R,4S,5S)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-(4-{(2R,3S,5R)-3-hydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-2-yl}-1H-1,2,3-triazol-1-yl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione; With pyridine; 1H-tetrazole; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve;

β-cyanoethoxy-N,N,N',N'-tetramethylphosphorodiamidite; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.bioorg.2011.03.002

Reference yield: 49.0%

1-[(2R,4S,5S)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-(4-{(2R,3S,5R)-3-hydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-2-yl}-1H-1,2,3-triazol-1-yl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione (1262311-81-8) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → (2R,3S,5R)-2-({1-[(2S,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl]}-1H-1,2,3-triazol-4-yl)-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite (1262311-78-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0030-1258243

Reference yield:

C27H30N2O4Si (1210349-14-6) → (2R,3S,5R)-2-({1-[(2S,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl]}-1H-1,2,3-triazol-4-yl)-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-3-yl 2-cyanoethyl diisopropylphosphoramidite (1262311-78-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; copper(II) sulfate / dichloromethane; water

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: pyridine; 1H-tetrazole / dichloromethane / 0.5 h / 20 °C / Molecular sieve

3.2: 0.5 h / 20 °C

With pyridine; 1H-tetrazole; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate; tetrabutyl ammonium fluoride; copper(II) sulfate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.bioorg.2011.03.002

upstream raw materials:

1-[(2R,4S,5S)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-(4-{(2R,3S,5R)-3-hydroxy-5-[5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]tetrahydrofuran-2-yl}-1H-1,2,3-triazol-1-yl)tetrahydrofuran-2-yl]-5-methylpyrimidine-2,4(1H,3H)-dione

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

C₂₇H₃₀N₂O₄Si

β-cyanoethoxy-N,N,N',N'-tetramethylphosphorodiamidite

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