Benzoic acid (2R,3S,4R)-5-acetoxy-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R)-5-acetoxy-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester
• CAS No.: 189748-69-4
• Molecular Formula: C₂₀H₂₉N₃O₅SSi
• Molecular Weight: 451.619

Synonyms:Benzoic acid (2R,3S,4R)-5-acetoxy-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester

Chemical Property of Benzoic acid (2R,3S,4R)-5-acetoxy-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4R)-5-acetoxy-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester

There total 10 articles about Benzoic acid (2R,3S,4R)-5-acetoxy-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-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:

tert-butyldimethylsilyl chloride (18162-48-6) → Benzoic acid (2R,3S,4R)-5-acetoxy-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester (189748-69-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / imidazole / dimethylformamide / Ambient temperature

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

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

4: 816 mg / 1.5 h / 100 °C

With 1H-imidazole; diphenylphosphoranyl azide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo9700540

Reference yield:

(3S,4S,5R)-4-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol (174833-54-6) → Benzoic acid (2R,3S,4R)-5-acetoxy-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester (189748-69-4)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; 1H-imidazole; dmap; ammonium fluoride; diphenylphosphoranyl azide; hydrogen fluoride; boron trichloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo9700540

Reference yield:

2,5-dideoxy-2,5-epithio-3-O-benzyl-D-lyxofuranoside (347362-38-3) → Benzoic acid (2R,3S,4R)-5-acetoxy-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester (189748-69-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) HCl, 2.) NaBH₄ / 1.) THF, water, room temperature, 1 h, 2.) methanol, 0 deg C, 45 min

2: 87 percent / imidazole / dimethylformamide / Ambient temperature

3: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

4: BCl₃ / CH₂Cl₂ / 6.5 h / -78 °C

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

6: 89 percent / NH₄F*HF / methanol / 43 h / Ambient temperature

7: 80 percent / imidazole / dimethylformamide / Ambient temperature

8: 83 percent / diphenylphosphoryl azide, diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2 h / Ambient temperature

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

10: 816 mg / 1.5 h / 100 °C

With pyridine; 1H-imidazole; hydrogenchloride; dmap; ammonium fluoride; sodium tetrahydroborate; diphenylphosphoranyl azide; hydrogen fluoride; boron trichloride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo9700540

upstream raw materials:

acetic anhydride

Benzoic acid (2R,3S,4R)-4-azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-1-oxo-tetrahydro-1λ⁴-thiophen-3-yl ester

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

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

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

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