(2R,3R)-3-{(1R)-1-[tert-butyl(dimethyl)siloxy]ethyl}-1-(diphenylmethyl)-4-oxoazetidine-2-yl acetate

Base Information

Chemical Name:(2R,3R)-3-{(1R)-1-[tert-butyl(dimethyl)siloxy]ethyl}-1-(diphenylmethyl)-4-oxoazetidine-2-yl acetate
CAS No.:1301239-57-5
Molecular Formula:C₂₆H₃₅NO₄Si
Molecular Weight:453.654
Hs Code.:

Synonyms:(2R,3R)-3-{(1R)-1-[tert-butyl(dimethyl)siloxy]ethyl}-1-(diphenylmethyl)-4-oxoazetidine-2-yl acetate

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Chemical Property of (2R,3R)-3-{(1R)-1-[tert-butyl(dimethyl)siloxy]ethyl}-1-(diphenylmethyl)-4-oxoazetidine-2-yl acetate

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Technology Process of (2R,3R)-3-{(1R)-1-[tert-butyl(dimethyl)siloxy]ethyl}-1-(diphenylmethyl)-4-oxoazetidine-2-yl acetate

There total 10 articles about (2R,3R)-3-{(1R)-1-[tert-butyl(dimethyl)siloxy]ethyl}-1-(diphenylmethyl)-4-oxoazetidine-2-yl acetate 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: 82.0%

: 1301239-55-3
(2R,3R)-1-(diphenylmethyl)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidine-2-yl acetate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1301239-57-5
(2R,3R)-3-{(1R)-1-[tert-butyl(dimethyl)siloxy]ethyl}-1-(diphenylmethyl)-4-oxoazetidine-2-yl acetate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;
DOI:10.1055/s-0030-1258407

Reference yield:

: 1301239-48-4
(3S,4S)-3-acetyl-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)azetidin-2-one

: 1301239-57-5
(2R,3R)-3-{(1R)-1-[tert-butyl(dimethyl)siloxy]ethyl}-1-(diphenylmethyl)-4-oxoazetidine-2-yl acetate

Guidance literature:: Multi-step reaction with 8 steps

1.1: titanium tetrachloride / dichloromethane / 0.17 h / -78 °C

1.2: 0.25 h / -78 °C

2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 2.5 h / 20 °C

3.1: potassium carbonate / methanol / 0.5 h / 20 °C

4.1: sulfuric acid / methanol / 24 h / 20 °C

5.1: sodium periodate; silica gel / dichloromethane / 72 h / 20 °C

6.1: potassium permanganate; potassium carbonate / tetrahydrofuran; water / 12 h / 20 °C

7.1: lead(IV) tetraacetate; acetic acid / N,N-dimethyl-formamide / 2 h / 65 °C / Inert atmosphere

8.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

With 1H-imidazole; potassium permanganate; sodium periodate; sulfuric acid; lead(IV) tetraacetate; silica gel; titanium tetrachloride; potassium carbonate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Mitsunobu reaction;
DOI:10.1055/s-0030-1258407

Reference yield:

: 1017251-76-1
(3S,4S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)-3-[(1S)-1-hydroxyethyl]azetidin-2-one

: 1301239-57-5
(2R,3R)-3-{(1R)-1-[tert-butyl(dimethyl)siloxy]ethyl}-1-(diphenylmethyl)-4-oxoazetidine-2-yl acetate

Guidance literature:: Multi-step reaction with 7 steps

1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 2.5 h / 20 °C

2: potassium carbonate / methanol / 0.5 h / 20 °C

3: sulfuric acid / methanol / 24 h / 20 °C

4: sodium periodate; silica gel / dichloromethane / 72 h / 20 °C

5: potassium permanganate; potassium carbonate / tetrahydrofuran; water / 12 h / 20 °C

6: lead(IV) tetraacetate; acetic acid / N,N-dimethyl-formamide / 2 h / 65 °C / Inert atmosphere

7: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C

With 1H-imidazole; potassium permanganate; sodium periodate; sulfuric acid; lead(IV) tetraacetate; silica gel; potassium carbonate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Mitsunobu reaction;
DOI:10.1055/s-0030-1258407