(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate
• CAS No.: 52523-24-7
• Molecular Formula: C₃₀H₂₄N₂O₈
• Molecular Weight: 540.529

Synonyms:(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate

Chemical Property of (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate

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Technology Process of (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate

There total 2 articles about (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate 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: 74.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 2-pyrimidinone hydrochloride (38353-09-2,1450-92-6) → (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate (52523-24-7)

Guidance literature:

With chloro-trimethyl-silane; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane; In acetonitrile;

DOI:10.1016/S0040-4039(00)76768-2

Reference yield: 45.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 2-(2-(trimethylsilyl)ethoxy)pyrimidine → (2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate (52523-24-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 25 ℃; for 1.5h; Inert atmosphere;

Reference yield: 94.0%

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate (52523-24-7) → Zebularine (3690-10-6,6710-48-1,6880-76-8,39598-12-4,63527-47-9,65025-03-8,65025-05-0)

Guidance literature:

With ammonia; In methanol; at 0 - 25 ℃;

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

2-pyrimidinone hydrochloride

Downstream raw materials:

1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)hexahydropyrimidin-2-one

C₃₀H₂₆N₂O₈

C₃₀H₂₆N₂O₈

Zebularine

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