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

Base Information

Chemical Name:N-[2-((5R,6S)-5-(tert-butyldimethylsilyloxy)-6-hydroxycyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide
CAS No.:1257051-36-7
Molecular Formula:C₂₁H₃₃N₃O₈SSi
Molecular Weight:515.66
Hs Code.:

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

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

Chemical Property:

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

There total 8 articles about N-[2-((5R,6S)-5-(tert-butyldimethylsilyloxy)-6-hydroxycyclohex-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: 97.0%

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

: 1257051-36-7
N-[2-((5R,6S)-5-(tert-butyldimethylsilyloxy)-6-hydroxycyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In tetrahydrofuran; at -40 - 0 ℃; diastereoselective reaction;
DOI:10.1002/asia.201000458

Reference yield:

: 1257051-31-2
3-cyclopentenylpropyl methanesulfonate

: 1257051-36-7
N-[2-((5R,6S)-5-(tert-butyldimethylsilyloxy)-6-hydroxycyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

Guidance literature:: Multi-step reaction with 7 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

7.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran / -40 - 0 °C

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; cerium(III) chloride heptahydrate; sodium hydrogencarbonate; ozone; triethylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; toluene; 3.3: Aldol condensation / 4.2: Rubottom oxidation / 7.1: Luche reduction;
DOI:10.1002/asia.201000458

Reference yield:

: C₉H₁₇N

: 1257051-36-7
N-[2-((5R,6S)-5-(tert-butyldimethylsilyloxy)-6-hydroxycyclohex-1-enyl)ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

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

2.1: ozone / toluene / 0 °C

2.2: 0.5 h / 20 °C

2.3: 2 h / 80 °C

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

3.2: 0.5 h / 20 °C

4.1: pyridine / 1 h / 20 °C

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

5.2: 0.5 h / 0 °C

6.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran / -40 - 0 °C

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; cerium(III) chloride heptahydrate; sodium hydrogencarbonate; ozone; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; water; toluene; 2.3: Aldol condensation / 3.2: Rubottom oxidation / 6.1: Luche reduction;
DOI:10.1002/asia.201000458