Benzoic acid (2R,3S,4R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,4R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester
CAS No.:189748-73-0
Molecular Formula:C₁₈H₁₈N₆O₅S
Molecular Weight:430.444
Hs Code.:

Synonyms:Benzoic acid (2R,3S,4R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester

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Chemical Property of Benzoic acid (2R,3S,4R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester

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Technology Process of Benzoic acid (2R,3S,4R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester

There total 12 articles about Benzoic acid (2R,3S,4R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-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: 45.0%

: 189748-72-9
Benzoic acid (2R,3S,4R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester

: 189748-73-0
Benzoic acid (2R,3S,4R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester

: 189748-74-1
Benzoic acid (2R,3S,4R,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester

Guidance literature:: With ammonium fluoride; hydrogen fluoride; In methanol; Ambient temperature;
DOI:10.1021/jo9700540

Reference yield:

: 160882-25-7
3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose

: 189748-73-0
Benzoic acid (2R,3S,4R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 87 percent / imidazole / dimethylformamide / Ambient temperature

2: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

3: BCl₃ / CH₂Cl₂ / 6.5 h / -78 °C

4: 4.01 g / triethylamine, 4-(dimethylamino)pyridine / acetonitrile / 5 h / Ambient temperature

5: 89 percent / NH₄F*HF / methanol / 43 h / Ambient temperature

6: 80 percent / imidazole / dimethylformamide / Ambient temperature

7: 83 percent / diphenylphosphoryl azide, diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2 h / Ambient temperature

8: m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / -78 °C

9: 816 mg / 1.5 h / 100 °C

10: 47 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 1.) 0 deg C, 1 h, 2.) room temperature, overnight

11: 43 percent / NH₄F*HF / methanol / Ambient temperature

With pyridine; 1H-imidazole; dmap; ammonium fluoride; trimethylsilyl trifluoromethanesulfonate; diphenylphosphoranyl azide; hydrogen fluoride; boron trichloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo9700540

Reference yield:

: 174833-54-6
(3S,4S,5R)-4-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol

: 189748-73-0
Benzoic acid (2R,3S,4R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: BCl₃ / CH₂Cl₂ / 6.5 h / -78 °C

3: 4.01 g / triethylamine, 4-(dimethylamino)pyridine / acetonitrile / 5 h / Ambient temperature

4: 89 percent / NH₄F*HF / methanol / 43 h / Ambient temperature

5: 80 percent / imidazole / dimethylformamide / Ambient temperature

6: 83 percent / diphenylphosphoryl azide, diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2 h / Ambient temperature

7: m-chloroperoxybenzoic acid / CH₂Cl₂ / 1 h / -78 °C

8: 816 mg / 1.5 h / 100 °C

9: 47 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 1.) 0 deg C, 1 h, 2.) room temperature, overnight

10: 43 percent / NH₄F*HF / methanol / Ambient temperature

With pyridine; 1H-imidazole; dmap; ammonium fluoride; trimethylsilyl trifluoromethanesulfonate; diphenylphosphoranyl azide; hydrogen fluoride; boron trichloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo9700540