N-[2-((R)-5-(tert-butyldimethylsilyloxy)-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

Base Information

Chemical Name:N-[2-((R)-5-(tert-butyldimethylsilyloxy)-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide
CAS No.:1257051-35-6
Molecular Formula:C₂₁H₃₁N₃O₈SSi
Molecular Weight:513.644
Hs Code.:

Synonyms:N-[2-((R)-5-(tert-butyldimethylsilyloxy)-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

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Chemical Property of N-[2-((R)-5-(tert-butyldimethylsilyloxy)-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

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Technology Process of N-[2-((R)-5-(tert-butyldimethylsilyloxy)-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

There total 7 articles about N-[2-((R)-5-(tert-butyldimethylsilyloxy)-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide 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:

: 1257051-34-5
N-[2-(5-acetoxy-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

: 69739-34-0
t-butyldimethylsiyl triflate

: C₁₇H₁₉N₃O₉S

: 1257051-35-6
N-[2-((R)-5-(tert-butyldimethylsilyloxy)-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

Guidance literature:: N-[2-(5-acetoxy-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide; In tetrahydrofuran; water; at 20 ℃; for 24h; pH=7.41; aq. phosphate buffer; Enzymatic reaction;

t-butyldimethylsiyl triflate; With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h; optical yield given as %ee;
DOI:10.1002/asia.201000458

Reference yield:

: 1257051-31-2
3-cyclopentenylpropyl methanesulfonate

: 1257051-35-6
N-[2-((R)-5-(tert-butyldimethylsilyloxy)-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: methanol / 3 h / Reflux

2.1: sodium hydrogencarbonate / dichloromethane; water / 0.5 h / 20 °C

3.1: ozone / toluene / 0 °C

3.2: 0.5 h / 20 °C

3.3: 2 h / 80 °C

4.1: trimethylsilyl trifluoromethanesulfonate; triethylamine / dichloromethane / 0.05 h / 0 °C

4.2: 0.5 h / 20 °C

5.1: pyridine / 1 h / 20 °C

6.1: lipase AK / tetrahydrofuran; water / 24 h / 20 °C / pH 7.41 / aq. phosphate buffer; Enzymatic reaction

6.2: 0.5 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; sodium hydrogencarbonate; ozone; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; toluene; 3.3: Aldol condensation / 4.2: Rubottom oxidation;
DOI:10.1002/asia.201000458

Reference yield:

: 1257051-32-3
N-(3-cyclopentenylpropyl)-N-methyl-2,4-dinitrobenzenesulfonamide

: 1257051-35-6
N-[2-((R)-5-(tert-butyldimethylsilyloxy)-6-oxocyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: ozone / toluene / 0 °C

1.2: 0.5 h / 20 °C

1.3: 2 h / 80 °C

2.1: trimethylsilyl trifluoromethanesulfonate; triethylamine / dichloromethane / 0.05 h / 0 °C

2.2: 0.5 h / 20 °C

3.1: pyridine / 1 h / 20 °C

4.1: lipase AK / tetrahydrofuran; water / 24 h / 20 °C / pH 7.41 / aq. phosphate buffer; Enzymatic reaction

4.2: 0.5 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; ozone; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; water; toluene; 1.3: Aldol condensation / 2.2: Rubottom oxidation;
DOI:10.1002/asia.201000458