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

Base Information

Chemical Name:(3S,4S)-4-benzyloxycarbonyl-1-[3'-(benzyloxycarbonyl)phenylacetate]-3-[4'-(tert-butyldiphenylsilyloxy)benzyl]-2-azetidionone
CAS No.:342624-75-3
Molecular Formula:C₅₀H₄₇NO₇Si
Molecular Weight:802.011
Hs Code.:

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

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

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

There total 17 articles about (3S,4S)-4-benzyloxycarbonyl-1-[3'-(benzyloxycarbonyl)phenylacetate]-3-[4'-(tert-butyldiphenylsilyloxy)benzyl]-2-azetidionone 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: 45.0%

: 193959-34-1
(3-benzyloxycarbonyl)phenylacetyl chloride

: 193959-26-1
(3S,4S)-3-[4-[(1,1-dimethylethyl)diphenylsilyloxy]phenylmethyl]-4-benzyloxycarbonylazetidin-2-one

: 342624-75-3
(3S,4S)-4-benzyloxycarbonyl-1-[3'-(benzyloxycarbonyl)phenylacetate]-3-[4'-(tert-butyldiphenylsilyloxy)benzyl]-2-azetidionone

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; 1.) -78 deg C, 2.) -78 deg C to room temperature;
DOI:10.1016/S0960-894X(97)00285-0

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

: 342624-75-3
(3S,4S)-4-benzyloxycarbonyl-1-[3'-(benzyloxycarbonyl)phenylacetate]-3-[4'-(tert-butyldiphenylsilyloxy)benzyl]-2-azetidionone

Guidance literature:: Multi-step reaction with 4 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

4.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / -78 °C

4.2: 45 percent / tetrahydrofuran / 2 h / -78 °C

With hydrogen fluoride; hydrogen; sodium hexamethyldisilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jm000145g

Reference yield:

: 116748-05-1
4-(tert-butyldiphenylsilyloxy)benzaldehyde

: 342624-75-3
(3S,4S)-4-benzyloxycarbonyl-1-[3'-(benzyloxycarbonyl)phenylacetate]-3-[4'-(tert-butyldiphenylsilyloxy)benzyl]-2-azetidionone

Guidance literature:: Multi-step reaction with 5 steps

1.1: LDA / tetrahydrofuran; hexane / 0.25 h / -9 °C

1.2: LDA / tetrahydrofuran; hexane / 0.33 h / -9 °C

1.3: tetrahydrofuran; hexane / 1 h / 0 °C

2.1: 13 percent / EDCI / DMAP / CH₂Cl₂ / 3 h / 20 °C

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

3.2: 33 percent / EDCI / DMAP / CH₂Cl₂ / 14 h

4.1: 93 percent / aq. HF / acetonitrile / 0.33 h / 20 °C

5.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / -78 °C

5.2: 45 percent / tetrahydrofuran / 2 h / -78 °C

With hydrogen fluoride; hydrogen; sodium hexamethyldisilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; dmap; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 1.1: Peterson reaction;
DOI:10.1021/jm000145g