4-bromo-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-5-oxiranyl-1,3-dioxolan-4-yl)ethyl]benzamide

Base Information

Chemical Name:4-bromo-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-5-oxiranyl-1,3-dioxolan-4-yl)ethyl]benzamide
CAS No.:1360594-48-4
Molecular Formula:C₃₂H₄₀BrNO₅Si
Molecular Weight:626.663
Hs Code.:

Synonyms:4-bromo-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-5-oxiranyl-1,3-dioxolan-4-yl)ethyl]benzamide

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Chemical Property of 4-bromo-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-5-oxiranyl-1,3-dioxolan-4-yl)ethyl]benzamide

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Technology Process of 4-bromo-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-5-oxiranyl-1,3-dioxolan-4-yl)ethyl]benzamide

There total 7 articles about 4-bromo-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-5-oxiranyl-1,3-dioxolan-4-yl)ethyl]benzamide 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: 98.0%

: 1360594-47-3
(S)-1-{(4R,5R)-5-[(S)-1-amino-2-(tert-butyldiphenylsilyloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethanol

: 586-75-4
4-chlorobenzoyl chloride

: 1360594-48-4
4-bromo-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-5-oxiranyl-1,3-dioxolan-4-yl)ethyl]benzamide

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1002/ejoc.201100968

Reference yield:

: 1138325-27-5
(R)-2-(benzyloxy)-1-((4S,5S)-5-((R)-2-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate

: 1360594-48-4
4-bromo-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-5-oxiranyl-1,3-dioxolan-4-yl)ethyl]benzamide

Guidance literature:: Multi-step reaction with 6 steps

1: palladium 10% on activated carbon; hydrogen / ethanol / 72 h / 3102.97 Torr

2: potassium carbonate / methanol / 20 °C / Inert atmosphere

3: pyridine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

4: sodium azide / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

5: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 760.05 Torr

6: triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

With pyridine; sodium azide; palladium 10% on activated carbon; hydrogen; potassium carbonate; triethylamine; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201100968

Reference yield:

: 1138325-28-6
(R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate

: 1360594-48-4
4-bromo-N-[2-(tert-butyldiphenylsilyloxy)-1-(2,2-dimethyl-5-oxiranyl-1,3-dioxolan-4-yl)ethyl]benzamide

Guidance literature:: Multi-step reaction with 5 steps

1: potassium carbonate / methanol / 20 °C / Inert atmosphere

2: pyridine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

4: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 760.05 Torr

5: triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

With pyridine; sodium azide; palladium 10% on activated carbon; hydrogen; potassium carbonate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201100968