3-[1-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(1H-1,2,3-triazol-1-yl)azetidin-2-one

Base Information

Chemical Name:3-[1-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(1H-1,2,3-triazol-1-yl)azetidin-2-one
CAS No.:247188-89-2
Molecular Formula:C₂₃H₃₀N₈O₆Si
Molecular Weight:542.627
Hs Code.:

Synonyms:3-[1-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(1H-1,2,3-triazol-1-yl)azetidin-2-one

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Chemical Property of 3-[1-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(1H-1,2,3-triazol-1-yl)azetidin-2-one

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Technology Process of 3-[1-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(1H-1,2,3-triazol-1-yl)azetidin-2-one

There total 7 articles about 3-[1-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(1H-1,2,3-triazol-1-yl)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: 70.0%

: 247188-88-1
3-[1-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-4-(1H-1,2,3-triazol-1-yl)azetidin-2-one

: 4457-32-3
4-nitrobenzyl chloroformate

: 247188-89-2
3-[1-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(1H-1,2,3-triazol-1-yl)azetidin-2-one

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1007/BF02256811

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 247188-89-2
3-[1-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(1H-1,2,3-triazol-1-yl)azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / imidazole / CH₂Cl₂ / 28 h / 20 °C

2: 92 percent / acetic acid / 1.5 h / 90 °C

3: 750 mg / KMnO₄; NaIO₄ / acetone; H₂O; aq. phosphate buffer / 20 °C / pH 7.0

4: 84 percent / NaN₃ / H₂O; acetone / 22 h / 50 °C

5: 87 percent / 1,2-dimethoxy-ethane / 22 h / 90 °C

6: 70 percent / Et₃N / CH₂Cl₂ / 20 °C

With 1H-imidazole; potassium permanganate; sodium periodate; sodium azide; triethylamine; In 1,2-dimethoxyethane; phosphate buffer; dichloromethane; water; acetic acid; acetone; 1: Substitution / 2: Ring cleavage / 3: Oxidation / 4: Substitution / 5: Cycloaddition / 6: Acylation;
DOI:10.1007/BF02256811

Reference yield:

: methyl 6-[1-hydroxy-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]penicillanate

: 247188-89-2
3-[1-(tert-butyldimethylsilyloxy)-1-(1-methyl-1H-1,2,3-triazol-4-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(1H-1,2,3-triazol-1-yl)azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / imidazole / CH₂Cl₂ / 28 h / 20 °C

2: 92 percent / acetic acid / 1.5 h / 90 °C

3: 750 mg / KMnO₄; NaIO₄ / acetone; H₂O; aq. phosphate buffer / 20 °C / pH 7.0

4: 84 percent / NaN₃ / H₂O; acetone / 22 h / 50 °C

5: 87 percent / 1,2-dimethoxy-ethane / 22 h / 90 °C

6: 70 percent / Et₃N / CH₂Cl₂ / 20 °C

With 1H-imidazole; potassium permanganate; sodium periodate; sodium azide; triethylamine; In 1,2-dimethoxyethane; phosphate buffer; dichloromethane; water; acetic acid; acetone; 1: Substitution / 2: Ring cleavage / 3: Oxidation / 4: Substitution / 5: Cycloaddition / 6: Acylation;
DOI:10.1007/BF02256811