(3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one

Base Information

Chemical Name:(3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one
CAS No.:182155-38-0
Molecular Formula:C₂₃H₂₉NO₃Si
Molecular Weight:395.574
Hs Code.:

Synonyms:(3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one

Chemical Property:

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Technology Process of (3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one

There total 9 articles about (3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-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: 65.0%

: 98-88-4
benzoyl chloride

: 182155-37-9
(3R,4S)-3-[(triethylsilyl)oxy]-4-(phenyl)-3-methyl-azetidinone

: 182155-38-0
(3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1016/0040-4039(96)01420-7

Reference yield:

: 994-30-9
triethylsilyl chloride

: 182155-38-0
(3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / imidazole / tetrahydrofuran / 16 h

2: 65 percent / i-Pr₂NEt, DMAP / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/0040-4039(96)01420-7

Reference yield:

: 132127-34-5
(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

: 182155-38-0
(3R,4S)-1-Benzoyl-3-methyl-4-phenyl-3-triethylsilanyloxy-azetidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 90 percent / PPTS / acetone / 20 h

2: 1.) LiHMDS / 1.) THF, -40 deg C, 2.) THF, -40 deg C, 2 h

3: 100 percent / 0.1N HCl / tetrahydrofuran / 1 h / Ambient temperature

4: 80 percent / Me₂S*Br₂ / CH₂Cl₂ / 2 h / 0 °C

5: 95 percent / tetrahydrofuran / 3 h / -40 °C

6: 90 percent / TBAF / tetrahydrofuran / 2 h / 0 °C

7: 91 percent / imidazole / tetrahydrofuran / 16 h

8: 65 percent / i-Pr₂NEt, DMAP / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; hydrogenchloride; dmap; tetrabutyl ammonium fluoride; dimethylsulfur dibromide; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1016/0040-4039(96)01420-7