(3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-benzylthiocarbonylethyl]-2-azetidinone

Base Information

Chemical Name:(3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-benzylthiocarbonylethyl]-2-azetidinone
CAS No.:163166-93-6
Molecular Formula:C₂₆H₃₉NO₅SSi
Molecular Weight:505.751
Hs Code.:

Synonyms:(3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-benzylthiocarbonylethyl]-2-azetidinone

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Chemical Property of (3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-benzylthiocarbonylethyl]-2-azetidinone

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Technology Process of (3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-benzylthiocarbonylethyl]-2-azetidinone

There total 5 articles about (3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-benzylthiocarbonylethyl]-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: 79.1%

: 100-53-8
phenylmethanethiol

: 153976-18-2
(3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-carboxyethyl]-2-azetidinone

: 163166-93-6
(3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-benzylthiocarbonylethyl]-2-azetidinone

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In benzene; at 25 ℃; for 17h;
DOI:10.1039/P19960002851

Reference yield:

: 93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2
(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

: 163166-93-6
(3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-benzylthiocarbonylethyl]-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / tetrahydrofuran / 1.) 10 deg C, 20 min, 2.) 25 deg C, 1 h

2: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -50 °C

3: aq. K₂CO₃ / tetrahydrofuran / 0.25 h / 25 °C

4: 79.1 percent / DCC, DMAP / benzene / 17 h / 25 °C

With dmap; sodium hexamethyldisilazane; sodium hydride; potassium carbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; benzene;
DOI:10.1039/P19960002851

Reference yield:

: 107514-91-0
(3S,4R)-3-<(1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<<(tert-butyldimethylsilyl)oxy>carbonyl>ethyl>azetidin-2-one

: 163166-93-6
(3S,4S)-1-(allyloxycarbonylmethyl)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(1R)-1-benzylthiocarbonylethyl]-2-azetidinone

Guidance literature:: Multi-step reaction with 3 steps

1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -50 °C

2: aq. K₂CO₃ / tetrahydrofuran / 0.25 h / 25 °C

3: 79.1 percent / DCC, DMAP / benzene / 17 h / 25 °C

With dmap; sodium hexamethyldisilazane; potassium carbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; benzene;
DOI:10.1039/P19960002851