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

Base Information

Chemical Name:(2R,3R)-1-(diphenylmethyl)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidine-2-yl acetate
CAS No.:1301239-55-3
Molecular Formula:C₂₀H₂₁NO₄
Molecular Weight:339.391
Hs Code.:

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

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Chemical Property of (2R,3R)-1-(diphenylmethyl)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidine-2-yl acetate

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Technology Process of (2R,3R)-1-(diphenylmethyl)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidine-2-yl acetate

There total 9 articles about (2R,3R)-1-(diphenylmethyl)-3-[(1R)-1-hydroxyethyl]-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: 72.0%

: 1301239-53-1
(2S,3S)-1-(diphenylmethyl)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidine-2-carboxylic acid

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

Guidance literature:: With lead(IV) tetraacetate; acetic acid; In N,N-dimethyl-formamide; at 65 ℃; for 2h; Inert atmosphere;
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

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

Guidance literature:: Multi-step reaction with 7 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

With 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

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

Guidance literature:: Multi-step reaction with 6 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

With 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