acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester

Base Information

Chemical Name:acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester
CAS No.:681811-46-1
Molecular Formula:C₂₀H₂₁N₃O₇
Molecular Weight:415.403
Hs Code.:

Synonyms:acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester

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Chemical Property of acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester

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Technology Process of acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester

There total 8 articles about acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester 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: 52.0%

: 681811-44-9
acetic acid (2R,3R,4S)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-benzyloxymethyltetrahydrofuran-3-yl ester

: 108-24-7
acetic anhydride

: 681811-46-1
acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester

Guidance literature:: acetic acid (2R,3R,4S)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-benzyloxymethyltetrahydrofuran-3-yl ester; With boron trichloride; In dichloromethane; at -78 ℃; for 2h;

acetic anhydride; With pyridine; at 20 ℃;
DOI:10.1016/j.bmc.2003.12.002

Reference yield:

: 681811-42-7
(2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-ol

: 681811-46-1
acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / pyridine; 4-(dimethylamino)pyridine / 1 h / 20 °C

2.1: ammonium sulfate; HMDS / 150 - 160 °C

2.2: 71 percent / TMSOTf / acetonitrile / 20 °C

3.1: BCl₃ / CH₂Cl₂ / 2 h / -78 °C

3.2: 52 percent / pyridine / 20 °C

With pyridine; dmap; ammonium sulfate; boron trichloride; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;
DOI:10.1016/j.bmc.2003.12.002

Reference yield:

: 681811-41-6
(-)-(3aR,6S,6aR)-6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

: 681811-46-1
acetic acid (2R,3R,4S)-4-acetoxymethyl-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)tetrahydrofuran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 75 percent / p-TsOH / 20 °C

2.1: 86 percent / pyridine; 4-(dimethylamino)pyridine / 1 h / 20 °C

3.1: ammonium sulfate; HMDS / 150 - 160 °C

3.2: 71 percent / TMSOTf / acetonitrile / 20 °C

4.1: BCl₃ / CH₂Cl₂ / 2 h / -78 °C

4.2: 52 percent / pyridine / 20 °C

With pyridine; dmap; ammonium sulfate; boron trichloride; toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;
DOI:10.1016/j.bmc.2003.12.002