4-Methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide

Base Information

Chemical Name:4-Methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide
CAS No.:150422-81-4
Molecular Formula:C₁₆H₂₃NO₅S
Molecular Weight:341.428
Hs Code.:

Synonyms:4-Methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide

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Chemical Property of 4-Methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide

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Technology Process of 4-Methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide

There total 14 articles about 4-Methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide 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: 73.0%

: 70-55-3
toluene-4-sulfonamide

: 135456-80-3
(Z)-(2R,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-enal

: 150422-81-4
4-Methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide

: 4-Methyl-N-((1S,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; 1.) -78 deg C, 1 h, 2.) -78 deg C to room temp., 1 h, 3.) room temp., 1 h;
DOI:10.1021/jo00070a016

Reference yield:

: 135456-73-4
O²,O³,O⁴-trimethyl-L-arabinose diethyl dithioacetal

: 150422-81-4
4-Methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / imidazole, DMAP / dimethylformamide / 16 h / Ambient temperature

2: 100 percent / HgO, HgCl₂ / acetone; H₂O / 1 h / 50 - 55 °C

3: 1.) t-BuOK, PPh₃ / 1.) toluene, -20 deg C, 15 min, 2.) toluene, -20 deg C to room temp., 30 min

4: 81 percent / n-BuLi, TMEDA / hexane; tetrahydrofuran / 1.) -78 deg C, 75 min, 2.) -78 deg C, 3 h, room temp., 3 h

5: 96 percent / H₂ / 5percent Pd/BaSO₄ / pyridine / 20 h / 760 Torr / Ambient temperature

6: 100 percent / aq. acetic acid / 12 h / Ambient temperature

7: 99 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h / -65 °C

8: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.) -78 dg C, 1 h, 2.) -78 deg C to room temp., 1 h, 3.) room temp., 1 h

With 1H-imidazole; dmap; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; acetic acid; dimethyl sulfoxide; triphenylphosphine; mercury dichloride; mercury(II) oxide; Pd-BaSO₄; In tetrahydrofuran; pyridine; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00070a016

Reference yield:

: 135456-75-6
(2R,3S,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3,4-trimethoxy-pentanal

: 150422-81-4
4-Methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) t-BuOK, PPh₃ / 1.) toluene, -20 deg C, 15 min, 2.) toluene, -20 deg C to room temp., 30 min

2: 81 percent / n-BuLi, TMEDA / hexane; tetrahydrofuran / 1.) -78 deg C, 75 min, 2.) -78 deg C, 3 h, room temp., 3 h

3: 96 percent / H₂ / 5percent Pd/BaSO₄ / pyridine / 20 h / 760 Torr / Ambient temperature

4: 100 percent / aq. acetic acid / 12 h / Ambient temperature

5: 99 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h / -65 °C

6: 73 percent / BF₃*OEt₂ / CH₂Cl₂ / 1.) -78 dg C, 1 h, 2.) -78 deg C to room temp., 1 h, 3.) room temp., 1 h

With n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; acetic acid; dimethyl sulfoxide; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; pyridine; hexane; dichloromethane;
DOI:10.1021/jo00070a016