(3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-2-azetidinone

Base Information

• Chemical Name: (3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-2-azetidinone
• CAS No.: 112256-77-6
• Molecular Formula: C₃₅H₄₇NO₅Si
• Molecular Weight: 589.847
• Mol file: 112256-77-6.mol

Synonyms:(3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-2-azetidinone

Chemical Property of (3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-2-azetidinone

There total 12 articles about (3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-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: 96.0%

(3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(R)-1-hydroxyethyl>-2-azetidinone (112256-78-7) + tert-butyldimethylsilyl chloride (18162-48-6) → (3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-2-azetidinone (112256-77-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1246/cl.1987.445

Reference yield:

(3S,4S)-3-acetyl-4-<(S)-1-benzyloxyethyl>-1-(di-p-anisylmethyl)-2-azetidinone (115026-43-2) → (3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-2-azetidinone (112256-77-6)

Guidance literature:

Multi-step reaction with 2 steps

2: 96 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1246/cl.1987.445

Reference yield:

bis(p-methoxyphenyl)methanone (90-96-0) → (3S,4S)-4-<(S)-1-benzyloxyethyl>-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-2-azetidinone (112256-77-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 2.) formamide, MgCl₂ / 1.) 180-190 deg C, 4 h; 2.) 180-190 deg C, 2 h

2: 8.48 g / 1M HCl / methanol / 2 h / Heating

3: MgSO₄ / toluene / 1 h / 0 °C

4: imidazole / CH₂Cl₂ / 69 h / -35 °C

5: 1M potassium triethylborohydride / tetrahydrofuran / 1 h / -78 °C

6: 91 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / Ambient temperature

7: 5.1 mg / K₂CO₃ / methanol / 0.17 h / Ambient temperature

8: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; dmap; potassium triethylborohydride; magnesium sulfate; potassium carbonate; formamide; triphenylphosphine; magnesium chloride; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)89105-5

upstream raw materials:

(3S,4S)-4-<(S)-1-benzyloxyethyl>-1--3-<(R)-1-hydroxyethyl>-2-azetidinone

tert-butyldimethylsilyl chloride

(3S,4S)-3-acetyl-4-<(S)-1-benzyloxyethyl>-1-(di-p-anisylmethyl)-2-azetidinone

bis(p-methoxyphenyl)methanone

Downstream raw materials:

(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-4-<(S)-1-hydroxyethyl>-2-azetidinone

(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-4-vinyl-2-azetidinone

(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-1-di-p-anisylmethyl-4-<(RS)-1-iodoethyl>-2-azetidinone

Toluene-4-sulfonic acid (S)-1-{(2S,3S)-1-[bis-(4-methoxy-phenyl)-methyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-ethyl ester