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

Base Information

• Chemical Name: (3S,4S)-3-acetyl-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)azetidin-2-one
• CAS No.: 1301239-48-4
• Molecular Formula: C₂₃H₂₅NO₄
• Molecular Weight: 379.456
• Mol file: 1301239-48-4.mol

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

Chemical Property of (3S,4S)-3-acetyl-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-acetyl-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)azetidin-2-one

There total 7 articles about (3S,4S)-3-acetyl-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)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: 68.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + {[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}-1,1-diphenylmethanamine (1301239-46-2) → (3S,4S)-3-acetyl-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)azetidin-2-one (1301239-48-4)

Guidance literature:

With 4-methyl-1H-imidazole; In tetrahydrofuran; at -78 ℃; for 168h; diastereoselective reaction;

DOI:10.1055/s-0030-1258407

Reference yield:

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + {[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}-1,1-diphenylmethanamine (1301239-46-2) → (3S,4S)-3-acetyl-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)azetidin-2-one (1301239-48-4) + (3R,4R)-3-acetyl-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)azetidin-2-one

Guidance literature:

With 1H-imidazole; In toluene; at -15 ℃; for 24h; optical yield given as %de;

DOI:10.1055/s-0030-1258407

Reference yield:

calcium bis[(2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)acetate] (98733-24-5) → (3S,4S)-3-acetyl-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)azetidin-2-one (1301239-48-4)

Guidance literature:

Multi-step reaction with 3 steps

1: calcium hypochlorite; sodium acetate; acetic acid / water / 0.58 h / 50 °C

2: magnesium sulfate / dichloromethane / 0.5 h / 20 °C

3: 4-methyl-1H-imidazole / tetrahydrofuran / 168 h / -78 °C

With calcium hypochlorite; 4-methyl-1H-imidazole; sodium acetate; magnesium sulfate; acetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1055/s-0030-1258407

upstream raw materials:

4-methyleneoxetan-2-one

{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methylene}-1,1-diphenylmethanamine

calcium bis[(2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)acetate]

(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Downstream raw materials:

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

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

(1R)-1-[(2S,3S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)-4-oxoazetidin-3-yl]ethyl benzoate

(1S)-1-[(2S,3S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(diphenylmethyl)-4-oxoazetidin-3-yl]ethyl methanesulfonate