3-[(2S,3R)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-azetidin-2-yl]-benzoic acid benzyl ester

Base Information

Chemical Name:3-[(2S,3R)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-azetidin-2-yl]-benzoic acid benzyl ester
CAS No.:253327-71-8
Molecular Formula:C₃₀H₃₃NO₅Si
Molecular Weight:515.681
Hs Code.:

Synonyms:3-[(2S,3R)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-azetidin-2-yl]-benzoic acid benzyl ester

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Chemical Property of 3-[(2S,3R)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-azetidin-2-yl]-benzoic acid benzyl ester

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Technology Process of 3-[(2S,3R)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-azetidin-2-yl]-benzoic acid benzyl ester

There total 8 articles about 3-[(2S,3R)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-azetidin-2-yl]-benzoic acid benzyl ester 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: 75.0%

: 98-88-4
benzoyl chloride

: 253327-70-7
3-[(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-oxo-azetidin-2-yl]-benzoic acid benzyl ester

: 253327-71-8
3-[(2S,3R)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-azetidin-2-yl]-benzoic acid benzyl ester

Guidance literature:: With triethylamine; In dichloromethane;
DOI:10.1016/S0960-894X(99)00522-3

Reference yield:

: 52010-98-7
3-(hydroxymethyl)benzaldehyde

: 253327-71-8
3-[(2S,3R)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-azetidin-2-yl]-benzoic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 82 percent / Et₃N / CH₂Cl₂

2: 100 percent / tetrahydrofuran

3: tetrahydrofuran / -78 - 20 °C

4: 88 percent / 0.25 percent aq. HCl / methanol

5: PDC

6: KMnO₄

7: 90 percent / DCC; DMAP / toluene

8: 75 percent / Et₃N / CH₂Cl₂

With hydrogenchloride; dmap; potassium permanganate; dipyridinium dichromate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: silylation / 2: amidosilylation / 3: asymmetric cyclocondensation / 4: Hydrolysis / 5: Oxidation / 6: Oxidation / 7: Esterification / 8: Acylation;
DOI:10.1016/S0960-894X(99)00522-3

Reference yield:

: 253327-65-0
3-triethylsilanyloxymethyl-benzaldehyde

: 253327-71-8
3-[(2S,3R)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-azetidin-2-yl]-benzoic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / tetrahydrofuran

2: tetrahydrofuran / -78 - 20 °C

3: 88 percent / 0.25 percent aq. HCl / methanol

4: PDC

5: KMnO₄

6: 90 percent / DCC; DMAP / toluene

7: 75 percent / Et₃N / CH₂Cl₂

With hydrogenchloride; dmap; potassium permanganate; dipyridinium dichromate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: amidosilylation / 2: asymmetric cyclocondensation / 3: Hydrolysis / 4: Oxidation / 5: Oxidation / 6: Esterification / 7: Acylation;
DOI:10.1016/S0960-894X(99)00522-3