(3S,4R)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one
• CAS No.: 122620-48-8
• Molecular Formula: C₂₂H₃₇NO₄Si
• Molecular Weight: 407.626
• Mol file: 122620-48-8.mol

Synonyms:(3S,4R)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

Chemical Property of (3S,4R)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one

There total 5 articles about (3S,4R)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-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:

(3R,4S)-5-Benzyloxy-3-hydroxy-4-methyl-pentanoic acid methoxy-amide (121534-58-5) → (3S,4R)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one (122620-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / DMAD / PPh₃ / tetrahydrofuran / 25 °C / different reaction partner

With DMAD; triphenylphosphine; In tetrahydrofuran;

DOI:10.1246/cl.1989.445

Reference yield:

(3R,4S)-5-Benzyloxy-3-hydroxy-4-methyl-pentanoic acid ethyl ester (120378-89-4) → (3S,4R)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one (122620-48-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / AlMe₃ / toluene / 25 °C

2: 92 percent / DMAD / PPh₃ / tetrahydrofuran / 25 °C / different reaction partner

With trimethylaluminum; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1246/cl.1989.445

Reference yield:

(2S)-3-(benzyloxy)-2-methylpropanal (79027-28-4) → (3S,4R)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methoxy-azetidin-2-one (122620-48-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / TiCl₄ / CH₂Cl₂ / -70 - -40 °C

2: 1.) imidazole 2.) AlMe₂ / 1.) DMF, 25 deg C, 2.) toluene, 25 deg C

3: 1.) MeSO₂Cl, 2.) K₂CO₃ / 1.) pyridine, 25 deg C, 2.) MeOH, 25 deg C

With 1H-imidazole; titanium tetrachloride; dimethylaluminum hydride; potassium carbonate; methanesulfonyl chloride; In dichloromethane;

DOI:10.1016/S0040-4039(00)82373-4

upstream raw materials:

C₂₇H₅₁NO₅Si₂

(S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-methoxy-azetidin-2-one

(3R,4S)-5-Benzyloxy-3-hydroxy-4-methyl-pentanoic acid methoxy-amide

(3R,4S)-5-Benzyloxy-3-hydroxy-4-methyl-pentanoic acid ethyl ester

Downstream raw materials:

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid