(S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

Base Information

• Chemical Name: (S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one
• CAS No.: 130422-42-3
• Molecular Formula: C₂₆H₃₇NO₅Si
• Molecular Weight: 471.669
• Mol file: 130422-42-3.mol

Synonyms:

Chemical Property of (S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

There total 10 articles about (S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one 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: 75.0%

3-Acetyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-(4-methoxy-phenyl)-azetidin-2-one (130422-43-4) → (S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one (130422-42-3,130467-68-4)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; L-Selectride; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)89035-8

Reference yield:

Benzyloxyacetyl chloride (19810-31-2) → (S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one (130422-42-3,130467-68-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent

3: 1.) LDA / 1.) THF, -78 deg C

4: 85 percent / PCC, NaOAc, mol. sieves (4 Angstroem)

5: 75 percent / L-Selectride, TMEDA / tetrahydrofuran / -78 °C

With N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; sodium acetate; L-Selectride; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)89035-8

Reference yield:

N-cinnamylidene-p-anisidine (80542-40-1) → (S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-3-((R)-1-hydroxy-ethyl)-1-(4-methoxy-phenyl)-azetidin-2-one (130422-42-3,130467-68-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent

3: 1.) LDA / 1.) THF, -78 deg C

4: 85 percent / PCC, NaOAc, mol. sieves (4 Angstroem)

5: 75 percent / L-Selectride, TMEDA / tetrahydrofuran / -78 °C

With N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; sodium acetate; L-Selectride; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)89035-8

upstream raw materials:

3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

acetaldehyde

Benzyloxyacetyl chloride

N-cinnamylidene-p-anisidine

Downstream raw materials:

3-Acetyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-1-(4-methoxy-phenyl)-azetidin-2-one

Toluene-4-sulfonic acid (R)-1-[(S)-3-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-1-(4-methoxy-phenyl)-4-oxo-azetidin-3-yl]-ethyl ester

Benzoic acid (S)-1-[(R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-1-(4-methoxy-phenyl)-4-oxo-3-(toluene-4-sulfonyloxy)-azetidin-3-yl]-ethyl ester

(2S,3S,6S)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-phenyl)-2-methyl-1-oxa-5-aza-spiro[2.3]hexan-4-one