(3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-hydroxy-ethyl)-azetidin-2-one

Base Information

Chemical Name:(3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-hydroxy-ethyl)-azetidin-2-one
CAS No.:194367-29-8
Molecular Formula:C₂₀H₃₃NO₃Si
Molecular Weight:363.572
Hs Code.:

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

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

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

There total 6 articles about (3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-hydroxy-ethyl)-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: 96.0%

: 161554-76-3
(3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-trityloxy-ethyl)-azetidin-2-one

: 194367-29-8
(3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-hydroxy-ethyl)-azetidin-2-one

Guidance literature:: With formic acid; In diethyl ether; for 0.116667h; Ambient temperature;
DOI:10.1021/jo970435d

Reference yield:

: 1026372-78-0
(2S,3S,4S)-3-Benzylamino-2-((R)-1-hydroxy-ethyl)-4-trityloxy-pentanoic acid tert-butyl ester

: 194367-29-8
(3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-hydroxy-ethyl)-azetidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: imidazole / CH₂Cl₂ / Ambient temperature

2: 81 percent / EtMgBr / tetrahydrofuran / 2 h / 0 °C

3: 96 percent / HCO₂H / diethyl ether / 0.12 h / Ambient temperature

With 1H-imidazole; formic acid; ethylmagnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo970435d

Reference yield:

: 161554-88-7
(E)-(S)-4-Trityloxy-pent-2-enoic acid tert-butyl ester

: 194367-29-8
(3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-hydroxy-ethyl)-azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1) THF, n-hexane, -78 deg C, 30 min; 2) THF, n-hexane, 1.5 h, -78 deg C

2: 1.) LDA / 1) THF, -78 deg C, 20 min; 2) THF, -78 deg C, 1.5 h

3: imidazole / CH₂Cl₂ / Ambient temperature

4: 81 percent / EtMgBr / tetrahydrofuran / 2 h / 0 °C

5: 96 percent / HCO₂H / diethyl ether / 0.12 h / Ambient temperature

With 1H-imidazole; n-butyllithium; formic acid; ethylmagnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo970435d