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

Base Information

Chemical Name:acetic acid (2R,3R,4S)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-benzyloxymethyltetrahydrofuran-3-yl ester
CAS No.:681811-44-9
Molecular Formula:C₂₅H₂₅N₃O₆
Molecular Weight:463.49
Hs Code.:

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

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

Chemical Property:

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

There total 8 articles about acetic acid (2R,3R,4S)-2-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-benzyloxymethyltetrahydrofuran-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: 71.0%

: 681811-43-8
acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester

: 26661-13-2
4-N-benzoylcytosine

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

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

Guidance literature:: 4-N-benzoylcytosine; With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane; at 150 - 160 ℃;

acetic acid (2RS,3R,4S)-4-benzyloxymethyl-2-methoxytetrahydrofuran-3-yl ester; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃;
DOI:10.1016/j.bmc.2003.12.002

Reference yield:

: dithiocarbonic acid O-(6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl) ester S-methyl ester

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1.82 g / Et₃B; nBu₃SnH / benzene; hexane / 3 h / 20 °C

2.1: 75 percent / p-TsOH / 20 °C

3.1: 86 percent / pyridine; 4-(dimethylamino)pyridine / 1 h / 20 °C

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

4.2: 71 percent / TMSOTf / acetonitrile / 20 °C

With pyridine; dmap; ammonium sulfate; triethyl borane; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In hexane; benzene;
DOI:10.1016/j.bmc.2003.12.002

Reference yield:

: 14048-35-2
(-)-(3aR,6S,6aR)-6-hydroxymethyl-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

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

Guidance literature:: Multi-step reaction with 6 steps

1.1: nBu₂SnO / toluene / 2 h / 140 - 150 °C

1.2: 73 percent / nBu₄NBr / toluene / 90 - 100 °C

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: tetrahydrofuran / 1 h / 20 °C

3.1: 1.82 g / Et₃B; nBu₃SnH / benzene; hexane / 3 h / 20 °C

4.1: 75 percent / p-TsOH / 20 °C

5.1: 86 percent / pyridine; 4-(dimethylamino)pyridine / 1 h / 20 °C

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

6.2: 71 percent / TMSOTf / acetonitrile / 20 °C

With pyridine; dmap; ammonium sulfate; triethyl borane; tri-n-butyl-tin hydride; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; toluene; benzene;
DOI:10.1016/j.bmc.2003.12.002