(3S,4S)-4-acetyl-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone

Base Information

• Chemical Name: (3S,4S)-4-acetyl-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone
• CAS No.: 97993-70-9
• Molecular Formula: C₂₁H₃₃NO₄Si
• Molecular Weight: 391.583
• Mol file: 97993-70-9.mol

Synonyms:(3S,4S)-4-acetyl-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone

Chemical Property of (3S,4S)-4-acetyl-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-acetyl-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone

There total 5 articles about (3S,4S)-4-acetyl-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-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:

[(4-Methoxy-benzyl)-amino]-acetic Acid Tert-butyl Ester (98076-56-3) → (3S,4S)-4-acetyl-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone (97993-70-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 71.5 percent / N,N'-dicyclohexylcarbodiimide / tetrahydrofuran / 0.5 h / 20 - 30 °C

2: n-BuLi, hexamethyldisilazane / tetrahydrofuran; hexane / 1) 1) 2 to 3 deg C, 2) 20 to 23 deg C, 30 min

3: 5percent NaHCO₃ / ethyl acetate

4: 1) 4-dimethylaminopyridine, 2) 1 M NaOH / 1) DMF, r.t., 16 h, 2) EtOH, 60 to 70 deg C, 2 h

5: 2) CuI / 1) THF, DMF, 0 deg C, 2) Et₂O, 0 deg C, 5 min; THF, -78 deg C, 15 min

With dmap; sodium hydroxide; copper(l) iodide; n-butyllithium; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; ethyl acetate;

DOI:10.1246/bcsj.58.3264

Reference yield:

(2S,3R)-N-(4-methoxybenzyl)-N-(t-butoxycarbonylmethyl)-2-bromo-3-hydroxybutyramide (98076-57-4) → (3S,4S)-4-acetyl-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone (97993-70-9)

Guidance literature:

Multi-step reaction with 4 steps

1: n-BuLi, hexamethyldisilazane / tetrahydrofuran; hexane / 1) 1) 2 to 3 deg C, 2) 20 to 23 deg C, 30 min

2: 5percent NaHCO₃ / ethyl acetate

3: 1) 4-dimethylaminopyridine, 2) 1 M NaOH / 1) DMF, r.t., 16 h, 2) EtOH, 60 to 70 deg C, 2 h

4: 2) CuI / 1) THF, DMF, 0 deg C, 2) Et₂O, 0 deg C, 5 min; THF, -78 deg C, 15 min

With dmap; sodium hydroxide; copper(l) iodide; n-butyllithium; sodium hydrogencarbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; ethyl acetate;

DOI:10.1246/bcsj.58.3264

Reference yield:

[(4-Methoxy-benzyl)-((2R,3R)-3-methyl-oxiranecarbonyl)-amino]-acetic acid tert-butyl ester → (3S,4S)-4-acetyl-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone (97993-70-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 5percent NaHCO₃ / ethyl acetate

2: 1) 4-dimethylaminopyridine, 2) 1 M NaOH / 1) DMF, r.t., 16 h, 2) EtOH, 60 to 70 deg C, 2 h

3: 2) CuI / 1) THF, DMF, 0 deg C, 2) Et₂O, 0 deg C, 5 min; THF, -78 deg C, 15 min

With dmap; sodium hydroxide; copper(l) iodide; sodium hydrogencarbonate; In ethyl acetate;

DOI:10.1246/bcsj.58.3264

upstream raw materials:

oxalyl dichloride

methyllithium

(2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxylic acid

[(4-Methoxy-benzyl)-amino]-acetic Acid Tert-butyl Ester

Downstream raw materials:

3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one

(3S,4R)-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone