N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-4-methylbenzenesulfonamide

Base Information

Chemical Name:N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-4-methylbenzenesulfonamide
CAS No.:872221-70-0
Molecular Formula:C₂₁H₂₉NO₄SSi
Molecular Weight:419.617
Hs Code.:

Synonyms:N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-4-methylbenzenesulfonamide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-4-methylbenzenesulfonamide

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Technology Process of N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-4-methylbenzenesulfonamide

There total 8 articles about N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-4-methylbenzenesulfonamide 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: 19.0%

: 922178-20-9
N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-N-propioloyl-4-methylbenzenesulfonamide

: 872221-70-0
N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-4-methylbenzenesulfonamide

: (1R,2S,6R)-4,4-dimethyl-12-methylene-14-(4-methylphenylsulfonyl)-11-trimethylsilyl-3,5-dioxa-14-azatricyclo-[7.5.0.0^2,6]tetradeca-7,9,10-trien-13-one

Guidance literature:: N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-N-propioloyl-4-methylbenzenesulfonamide; With n-butyllithium; In tetrahydrofuran;

With trimethylsilylacetylene; bis(triphenylphosphine)nickel(II) chloride; In tetrahydrofuran; at 50 ℃;
DOI:10.1139/V06-078

Reference yield:

: N-((1R,2R,5R,6S)-5,6-Dihydroxy-2-trimethylsilanylethynyl-cyclohex-3-enyl)-4-methyl-benzenesulfonamide

: 77-76-9
2,2-dimethoxy-propane

: 872221-70-0
N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 0.25h;
DOI:10.1021/ol052372o

Reference yield:

: 160309-18-2
(1R,4R,5S,6R)-4,5-(isopropylidenedioxy)-7-(4'-methylphenylsulfonyl)-7-azabicyclo<4.1.0>hept-2-ene

: 872221-70-0
N-[(1R,2R,5R,6S)-2-(2-trimethylsilylethynyl)-5,6-(isopropylidenedioxy)cyclohex-3-en-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / toluene / 0.17 h / 0 °C

1.2: AlCl₃ / toluene / 18 h / 0 - 20 °C

2.1: 2.14 mmol / p-toluenesulfonic acid / acetone / 0.25 h / 20 °C

With n-butyllithium; toluene-4-sulfonic acid; In acetone; toluene;
DOI:10.1139/V06-078