(3R,4S)-3-(tert-butyldimethylsilanyloxy)-4-(1-formyl-1,1-dimethylmethyl)-1-(4-methoxyphenyl)azetidin-2-one

Base Information

Chemical Name:(3R,4S)-3-(tert-butyldimethylsilanyloxy)-4-(1-formyl-1,1-dimethylmethyl)-1-(4-methoxyphenyl)azetidin-2-one
CAS No.:957791-72-9
Molecular Formula:C₂₀H₃₁NO₄Si
Molecular Weight:377.556
Hs Code.:

Synonyms:(3R,4S)-3-(tert-butyldimethylsilanyloxy)-4-(1-formyl-1,1-dimethylmethyl)-1-(4-methoxyphenyl)azetidin-2-one

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Chemical Property of (3R,4S)-3-(tert-butyldimethylsilanyloxy)-4-(1-formyl-1,1-dimethylmethyl)-1-(4-methoxyphenyl)azetidin-2-one

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Technology Process of (3R,4S)-3-(tert-butyldimethylsilanyloxy)-4-(1-formyl-1,1-dimethylmethyl)-1-(4-methoxyphenyl)azetidin-2-one

There total 10 articles about (3R,4S)-3-(tert-butyldimethylsilanyloxy)-4-(1-formyl-1,1-dimethylmethyl)-1-(4-methoxyphenyl)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: 83.0%

: 957791-70-7
(3R,4S)-3-(tert-butyldimethylsilanyloxy)-4-(1,1-dimethyl-2-hydroxy-ethyl)-1-(4-methoxyphenyl)azetidin-2-one

: 957791-72-9
(3R,4S)-3-(tert-butyldimethylsilanyloxy)-4-(1-formyl-1,1-dimethylmethyl)-1-(4-methoxyphenyl)azetidin-2-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -60 - 20 ℃; for 5h;
DOI:10.1016/j.tetasy.2007.08.012

Reference yield:

: 957791-54-7
(E)-N-(3-(benzyloxy)-2,2-dimethylpropylidene)-4-methoxybenzenamine

: 957791-72-9
(3R,4S)-3-(tert-butyldimethylsilanyloxy)-4-(1-formyl-1,1-dimethylmethyl)-1-(4-methoxyphenyl)azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / triethylamine / CH₂Cl₂ / -10 - 20 °C

2: 48 percent / Amano PS lipase / aq. phosphate buffer; acetonitrile / 72 h / 20 °C / pH 7.5

3: 92 percent / aq. KOH / tetrahydrofuran / 2 h / 0 °C

4: 97 percent / imidazole / dimethylformamide / 4 h / 35 °C

5: 57 percent / ammonium formate / palladium on activated carbon / methanol / 0.33 h / Heating

6: 83 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 5 h / -60 - 20 °C

With 1H-imidazole; potassium hydroxide; oxalyl dichloride; Amano PS Lipase; ammonium formate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6: Swern oxidation;
DOI:10.1016/j.tetasy.2007.08.012

Reference yield:

: 865154-54-7
(3R,4S)-3-hydroxy-4-(2-benzyloxy-1,1-dimethylethyl)-1-(4-methoxyphenyl)azetidin-2-one

: 957791-72-9
(3R,4S)-3-(tert-butyldimethylsilanyloxy)-4-(1-formyl-1,1-dimethylmethyl)-1-(4-methoxyphenyl)azetidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / imidazole / dimethylformamide / 4 h / 35 °C

2: 57 percent / ammonium formate / palladium on activated carbon / methanol / 0.33 h / Heating

3: 83 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 5 h / -60 - 20 °C

With 1H-imidazole; oxalyl dichloride; ammonium formate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; 3: Swern oxidation;
DOI:10.1016/j.tetasy.2007.08.012