(2S)-benzyl 2-(((3R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yloxy)(phenoxy)phosphorylamino)propanoate

Base Information

• Chemical Name: (2S)-benzyl 2-(((3R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yloxy)(phenoxy)phosphorylamino)propanoate
• CAS No.: 1333503-80-2
• Molecular Formula: C₂₅H₂₈N₃O₈P
• Molecular Weight: 529.486

Synonyms:(2S)-benzyl 2-(((3R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yloxy)(phenoxy)phosphorylamino)propanoate

Chemical Property of (2S)-benzyl 2-(((3R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yloxy)(phenoxy)phosphorylamino)propanoate

Chemical Property:

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Technology Process of (2S)-benzyl 2-(((3R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yloxy)(phenoxy)phosphorylamino)propanoate

There total 10 articles about (2S)-benzyl 2-(((3R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yloxy)(phenoxy)phosphorylamino)propanoate 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: 33.0%

1-((2R,4R)-tetrahydro-4-hydroxyfuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (1333503-71-1) + phenyl(benzyloxy-L-alaninyl)phosphorochloridate (183370-70-9) → (2S)-benzyl 2-(((3R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yloxy)(phenoxy)phosphorylamino)propanoate (1333503-80-2)

Guidance literature:

1-((2R,4R)-tetrahydro-4-hydroxyfuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione; With tert-butylmagnesium chloride; In tetrahydrofuran; for 0.5h; Inert atmosphere;

phenyl(benzyloxy-L-alaninyl)phosphorochloridate; In tetrahydrofuran; at 20 ℃; for 18h; Further stages; Inert atmosphere;

DOI:10.1016/j.ejmech.2011.05.036

Reference yield:

2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → (2S)-benzyl 2-(((3R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yloxy)(phenoxy)phosphorylamino)propanoate (1333503-80-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 4 h / 0 - 20 °C / Inert atmosphere

2.1: methanol; ammonia / 6 h / 20 °C / Inert atmosphere

3.1: dmap; p-Tolyl chlorothionoformate / acetonitrile / 0 - 20 °C / Inert atmosphere

3.2: 60 - 100 °C / Inert atmosphere

4.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1 h / 0 °C

5.1: tert-butylmagnesium chloride / tetrahydrofuran / 0.5 h / Inert atmosphere

5.2: 18 h / 20 °C / Inert atmosphere

With methanol; dmap; ammonium cerium (IV) nitrate; p-Tolyl chlorothionoformate; trimethylsilyl trifluoromethanesulfonate; tert-butylmagnesium chloride; ammonia; water; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile; 1.1: Vorbrüggen coupling / 3.1: Barton-McCombie deoxygenation / 3.2: Barton-McCombie deoxygenation;

DOI:10.1016/j.ejmech.2011.05.036

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → (2S)-benzyl 2-(((3R,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yloxy)(phenoxy)phosphorylamino)propanoate (1333503-80-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / 135 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 4 h / 0 - 20 °C / Inert atmosphere

3.1: methanol; ammonia / 6 h / 20 °C / Inert atmosphere

4.1: dmap; p-Tolyl chlorothionoformate / acetonitrile / 0 - 20 °C / Inert atmosphere

4.2: 60 - 100 °C / Inert atmosphere

5.1: ammonium cerium (IV) nitrate; water / acetonitrile / 1 h / 0 °C

6.1: tert-butylmagnesium chloride / tetrahydrofuran / 0.5 h / Inert atmosphere

6.2: 18 h / 20 °C / Inert atmosphere

With pyridine; methanol; dmap; ammonium cerium (IV) nitrate; p-Tolyl chlorothionoformate; trimethylsilyl trifluoromethanesulfonate; tert-butylmagnesium chloride; ammonia; water; In tetrahydrofuran; 1,2-dichloro-ethane; acetonitrile; 2.1: Vorbrüggen coupling / 4.1: Barton-McCombie deoxygenation / 4.2: Barton-McCombie deoxygenation;

DOI:10.1016/j.ejmech.2011.05.036

upstream raw materials:

(2R,3R,4S)-4-(benzyloxy)-tetrahydro-2-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)furan-3-yl acetate

(2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-2-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)furan-3-yl acetate

1-((2R,4R)-4-(benzyloxy)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

1-((2R,4R)-4-(4-methoxybenzyloxy)-tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

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