(S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

Base Information

• Chemical Name: (S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone
• CAS No.: 159622-41-0
• Molecular Formula: C₁₇H₂₇NO₃Si
• Molecular Weight: 321.492
• Mol file: 159622-41-0.mol

Synonyms:(S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

Chemical Property of (S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone

There total 9 articles about (S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone 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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (S) 4-<(4-methoxyphenoxy)methyl>-2-azetidinone (159622-40-9) → (S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone (159622-41-0)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h; 1.) 0 deg C;

DOI:10.1016/S0040-4020(01)89309-1

Reference yield:

2-(4-methoxyphenoxy)acetic acid (1877-75-4) → (S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone (159622-41-0)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine, N,N'-carboxyldiimidazole, 4-dimethylaminopyridine / CH₂Cl₂ / 0 deg C, 1 h; room temp., 5 h

2: toluene / 0.75 h / 85 °C

3: 69 percent / ethanol; H₂O / 30 h / baker's yeast, immobilized on calcium alignate, fermented at 29 deg C, wit sucrose

4: hydrogen / 10percent Pd/C / ethanol / 2 h

5: N-ethyl-N'-(3-dimethylaminopropyl)carboidimide / H₂O; tetrahydrofuran / 1 h

6: 80 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 0.5 h / Ambient temperature

7: hydrogen / 10percent Pd/C / methanol / 1 h

8: 30percent TiCl₃ / methanol; H₂O / 0.5 h / Ambient temperature; pH 7

9: 95 percent / Et₃N / dimethylformamide / 2 h / 20 °C / 1.) 0 deg C

With pyridine; dmap; titanium(III) chloride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)89309-1

Reference yield:

4-(4-Methoxy-phenoxy)-3-oxo-butyric acid (646034-68-6) → (S) 1-(tert-butyldimethysilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone (159622-41-0)

Guidance literature:

Multi-step reaction with 8 steps

1: toluene / 0.75 h / 85 °C

2: 69 percent / ethanol; H₂O / 30 h / baker's yeast, immobilized on calcium alignate, fermented at 29 deg C, wit sucrose

3: hydrogen / 10percent Pd/C / ethanol / 2 h

4: N-ethyl-N'-(3-dimethylaminopropyl)carboidimide / H₂O; tetrahydrofuran / 1 h

5: 80 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 0.5 h / Ambient temperature

6: hydrogen / 10percent Pd/C / methanol / 1 h

7: 30percent TiCl₃ / methanol; H₂O / 0.5 h / Ambient temperature; pH 7

8: 95 percent / Et₃N / dimethylformamide / 2 h / 20 °C / 1.) 0 deg C

With titanium(III) chloride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)89309-1

upstream raw materials:

tert-butyldimethylsilyl chloride

(S) 4-<(4-methoxyphenoxy)methyl>-2-azetidinone

2-(4-methoxyphenoxy)acetic acid

4-(4-Methoxy-phenoxy)-3-oxo-butyric acid

Downstream raw materials:

(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-hydroxymethyl-2-azetidinone

(3S,4S) 3-<(benzyloxycarbonyl)amino>-1-(tert-butyldimethylsilyl)-4-<(4-methoxyphenoxy)methyl>-2-azetidinone