2-Azetidinecarboxylic acid, 3-[[4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]phenyl]methyl]-4-oxo-, phenylmethyl ester, (2S,3S)-

Base Information

• Chemical Name: 2-Azetidinecarboxylic acid, 3-[[4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]phenyl]methyl]-4-oxo-, phenylmethyl ester, (2S,3S)-
• CAS No.: 193959-26-1
• Molecular Formula: C34H35NO4Si
• Molecular Weight: 549.742
• Mol file: 193959-26-1.mol

Synonyms:

Chemical Property of 2-Azetidinecarboxylic acid, 3-[[4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]phenyl]methyl]-4-oxo-, phenylmethyl ester, (2S,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Azetidinecarboxylic acid, 3-[[4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]phenyl]methyl]-4-oxo-, phenylmethyl ester, (2S,3S)-

There total 19 articles about 2-Azetidinecarboxylic acid, 3-[[4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]phenyl]methyl]-4-oxo-, phenylmethyl ester, (2S,3S)- 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: 93.0%

(3S,4S)-4-benzyloxycarbonyl-1-(tert-butyldimethylsilyl)-3-[4'-(tert-butyldiphenylsilyloxy)benzyl]-2-azetidinone (193959-25-0) → (3S,4S)-3-[4-[(1,1-dimethylethyl)diphenylsilyloxy]phenylmethyl]-4-benzyloxycarbonylazetidin-2-one (193959-26-1)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1016/S0960-894X(97)00285-0

Reference yield: 70.0%

(3S,4S)-1-(4-methoxyphenyl)-3-[4-[(1,1-dimethylethyl)diphenylsilyloxy]phenylmethyl]-4-benzyloxycarbonylazetidin-2-one (441786-70-5) → (3S,4S)-3-[4-[(1,1-dimethylethyl)diphenylsilyloxy]phenylmethyl]-4-benzyloxycarbonylazetidin-2-one (193959-26-1)

Guidance literature:

With ammonium cerium(IV) nitrate; In water; acetonitrile; at -20 - -10 ℃; for 0.5h;

DOI:10.1016/S0968-0896(02)00017-2

Reference yield:

(S)-1-(tert-Butyl-dimethyl-silanyl)-3-[1-[4-(tert-butyl-diphenyl-silanyloxy)-phenyl]-meth-(Z)-ylidene]-4-oxo-azetidine-2-carboxylic acid → (3S,4S)-3-[4-[(1,1-dimethylethyl)diphenylsilyloxy]phenylmethyl]-4-benzyloxycarbonylazetidin-2-one (193959-26-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 13 percent / EDCI / DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: H₂ / Pd/C / tetrahydrofuran / 30 h

2.2: 33 percent / EDCI / DMAP / CH₂Cl₂ / 14 h

3.1: 93 percent / aq. HF / acetonitrile / 0.33 h / 20 °C

With hydrogen fluoride; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/jm000145g

upstream raw materials:

(3S,4S)-4-benzyloxycarbonyl-1-(tert-butyldimethylsilyl)-3-[4'-(tert-butyldiphenylsilyloxy)benzyl]-2-azetidinone

(3S,4S)-1-(4-methoxyphenyl)-3-[4-[(1,1-dimethylethyl)diphenylsilyloxy]phenylmethyl]-4-benzyloxycarbonylazetidin-2-one

benzyl bromide

(3S,4S)-1-(4-methoxyphenyl)-3-[4-(2-propenyloxy)phenylmethyl]-4-formylazetidin-2-one

Downstream raw materials:

(3S,4S)-4-benzyloxycarbonyl-1-[3'-(benzyloxycarbonyl)phenylacetate]-3-[4'-(tert-butyldiphenylsilyloxy)benzyl]-2-azetidionone

(2S,3S)-1-[2-(3-Benzyloxycarbonyl-phenyl)-acetyl]-3-(4-hydroxy-benzyl)-4-oxo-azetidine-2-carboxylic acid benzyl ester