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

Base Information

• Chemical Name: (2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-2-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)furan-3-yl acetate
• CAS No.: 1333503-52-8
• Molecular Formula: C₁₉H₂₂N₂O₇
• Molecular Weight: 390.393

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

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

Chemical Property:

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

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

(3R,4S)-4-(4-methoxybenzyloxy)-tetrahydrofuran-2,3-diyl diacetate (1333503-49-3) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) → (2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-2-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)furan-3-yl acetate (1333503-52-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.ejmech.2011.05.036

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → (2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-2-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)furan-3-yl acetate (1333503-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 135 °C / Inert atmosphere

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

With pyridine; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; 2: Vorbrüggen coupling;

DOI:10.1016/j.ejmech.2011.05.036

Reference yield: 78.0%

(2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-2-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)furan-3-yl acetate (1333503-52-8) → 1-((2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-3-hydroxyfuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (1333503-58-4)

Guidance literature:

With methanol; ammonia; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.ejmech.2011.05.036

upstream raw materials:

(3R,4S)-4-(4-methoxybenzyloxy)-tetrahydrofuran-2,3-diyl diacetate

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

thymin

Downstream raw materials:

1-((2R,3R,4S)-4-(4-methoxybenzyloxy)-tetrahydro-3-hydroxyfuran-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

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

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