(2R,3R,4R,5R)‐5‐(4‐benzamido‐2‐oxo‐[5,6‐D₂]pyrimidin‐1(2H)‐yl)‐2‐((benzoyloxy)methyl)‐4‐fluoro‐4‐methyltetrahydrofuran‐3‐yl benzoate

Base Information

• Chemical Name: (2R,3R,4R,5R)‐5‐(4‐benzamido‐2‐oxo‐[5,6‐D₂]pyrimidin‐1(2H)‐yl)‐2‐((benzoyloxy)methyl)‐4‐fluoro‐4‐methyltetrahydrofuran‐3‐yl benzoate
• CAS No.: 1621160-32-4
• Molecular Formula: C₃₁H₂₆FN₃O₇
• Molecular Weight: 573.546

Synonyms:(2R,3R,4R,5R)‐5‐(4‐benzamido‐2‐oxo‐[5,6‐D₂]pyrimidin‐1(2H)‐yl)‐2‐((benzoyloxy)methyl)‐4‐fluoro‐4‐methyltetrahydrofuran‐3‐yl benzoate

Chemical Property of (2R,3R,4R,5R)‐5‐(4‐benzamido‐2‐oxo‐[5,6‐D₂]pyrimidin‐1(2H)‐yl)‐2‐((benzoyloxy)methyl)‐4‐fluoro‐4‐methyltetrahydrofuran‐3‐yl benzoate

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Technology Process of (2R,3R,4R,5R)‐5‐(4‐benzamido‐2‐oxo‐[5,6‐D₂]pyrimidin‐1(2H)‐yl)‐2‐((benzoyloxy)methyl)‐4‐fluoro‐4‐methyltetrahydrofuran‐3‐yl benzoate

There total 4 articles about (2R,3R,4R,5R)‐5‐(4‐benzamido‐2‐oxo‐[5,6‐D₂]pyrimidin‐1(2H)‐yl)‐2‐((benzoyloxy)methyl)‐4‐fluoro‐4‐methyltetrahydrofuran‐3‐yl benzoate 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:

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate (1500076-79-8) + N‐(2‐oxo‐1,2‐dihydro‐[5,6‐D2]pyrimidin‐4‐yl)benzamide (1621160-30-2) → (2R,3R,4R,5R)‐5‐(4‐benzamido‐2‐oxo‐[5,6‐D2]pyrimidin‐1(2H)‐yl)‐2‐((benzoyloxy)methyl)‐4‐fluoro‐4‐methyltetrahydrofuran‐3‐yl benzoate (1621160-32-4)

Guidance literature:

N‐(2‐oxo‐1,2‐dihydro‐[5,6‐D₂]pyrimidin‐4‐yl)benzamide; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; In chlorobenzene; at 140 ℃; for 1h;

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate; With tin(IV) chloride; In chlorobenzene; at 80 ℃; for 4h;

Reference yield:

(2R,3R,4R,5R)-5-acetoxy-2-((benzoyloxy)methyl)-4-fluoro-4-methyl-tetrahydrofuran-3-yl benzoate (874638-93-4) + C14H15(2)H2N3O2Si → (2R,3R,4R,5R)‐5‐(4‐benzamido‐2‐oxo‐[5,6‐D2]pyrimidin‐1(2H)‐yl)‐2‐((benzoyloxy)methyl)‐4‐fluoro‐4‐methyltetrahydrofuran‐3‐yl benzoate (1621160-32-4)

Guidance literature:

With titanium tetrachloride; In chlorobenzene; at 20 - 70 ℃; for 21h; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/jlcr.3715

Reference yield:

N‐(2‐oxo‐1,2‐dihydro‐[5,6‐D2]pyrimidin‐4‐yl)benzamide (1621160-30-2) → (2R,3R,4R,5R)‐5‐(4‐benzamido‐2‐oxo‐[5,6‐D2]pyrimidin‐1(2H)‐yl)‐2‐((benzoyloxy)methyl)‐4‐fluoro‐4‐methyltetrahydrofuran‐3‐yl benzoate (1621160-32-4)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium sulfate / 6 h / Reflux

2: titanium tetrachloride / chlorobenzene / 21 h / 20 - 70 °C / Inert atmosphere

With ammonium sulfate; titanium tetrachloride; In chlorobenzene;

DOI:10.1002/jlcr.3715

upstream raw materials:

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate

N‐(2‐oxo‐1,2‐dihydro‐[5,6‐D₂]pyrimidin‐4‐yl)benzamide

benzoyl chloride

(2R,3R,4R,5R)-5-acetoxy-2-((benzoyloxy)methyl)-4-fluoro-4-methyl-tetrahydrofuran-3-yl benzoate

Downstream raw materials:

((2R,3R,4R,5R)‐3‐(benzoyloxy)‐5‐(2,4‐dioxo‐3,4‐dihydro‐[5,6‐D₂]pyrimidin‐1(2H)‐yl)‐4‐fluoro‐4‐methyltetrahydrofuran‐2‐yl)methyl benzoate

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