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

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Chemical Name:(3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-trityloxy-ethyl)-azetidin-2-one
CAS No.:161554-76-3
Molecular Formula:C₃₉H₄₇NO₃Si
Molecular Weight:605.893
Hs Code.:

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

There total 9 articles about (3S,4S)-1-Benzyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((S)-1-trityloxy-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: 81.0%

: 161554-75-2
(2S,3S,4S)-3-Benzylamino-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-trityloxy-pentanoic acid tert-butyl ester

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

Guidance literature:: With ethylmagnesium bromide; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1016/S0040-4039(00)74424-8

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 194367-52-7
(3S,4S)-3-Benzylamino-4-trityloxy-pentanoic acid tert-butyl ester

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

Guidance literature:: Multi-step reaction with 3 steps

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

2: imidazole / CH₂Cl₂ / Ambient temperature

3: 81 percent / EtMgBr / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; ethylmagnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo970435d