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

Base Information

• Chemical Name: 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
• CAS No.: 130422-44-5
• Molecular Formula: C₃₃H₄₃NO₇SSi
• Molecular Weight: 625.858
• Mol file: 130422-44-5.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 7 articles about 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 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%

(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) + N-tosylimidazole (2232-08-8) → 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 (130422-44-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

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

Reference yield:

Benzyloxyacetyl chloride (19810-31-2) → 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 (130422-44-5)

Guidance literature:

Multi-step reaction with 6 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

6: 75 percent / NaH / dimethylformamide

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

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

Reference yield:

N-cinnamylidene-p-anisidine (80542-40-1) → 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 (130422-44-5)

Guidance literature:

Multi-step reaction with 6 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

6: 75 percent / NaH / dimethylformamide

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

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

upstream raw materials:

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

N-tosylimidazole

Benzyloxyacetyl chloride

N-cinnamylidene-p-anisidine

Downstream raw materials:

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