((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: ((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate
• CAS No.: 1234514-01-2
• Molecular Formula: C₂₅H₂₈O₇S
• Molecular Weight: 472.559
• Mol file: 1234514-01-2.mol

Synonyms:

Chemical Property of ((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate

There total 1 articles about ((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate 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:

C18H22O5 + p-toluenesulfonyl chloride (98-59-9) → ((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate (1234514-01-2)

Guidance literature:

With triethylamine; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tet.2010.04.048

Reference yield:

((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate (1234514-01-2) → N-benzyl-2-((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)acetamide

Guidance literature:

Multi-step reaction with 5 steps

1: sodium iodide / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere

2: copper(l) iodide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling

3: 2,6-dimethylpyridine; osmium(VIII) oxide; sodium periodate / water; 1,4-dioxane / 4 h / 20 °C

4: sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol; cyclohexene / 1 h / 20 °C

5: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / dichloromethane / 14 h / Inert atmosphere

With 2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; copper(l) iodide; osmium(VIII) oxide; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; sodium iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; cyclohexene;

DOI:10.1016/j.bmc.2013.09.052

Reference yield:

((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl 4-methylbenzenesulfonate (1234514-01-2) → 1-benzyl-5-(((1R,3R)-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-benzo[g]isochromen-3-yl)methyl)-1H-tetrazole

Guidance literature:

Multi-step reaction with 6 steps

1: sodium iodide / N,N-dimethyl-formamide / 6 h / 120 °C / Inert atmosphere

2: copper(l) iodide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / tetrahydrofuran / 20 °C / Inert atmosphere; Cooling

3: 2,6-dimethylpyridine; osmium(VIII) oxide; sodium periodate / water; 1,4-dioxane / 4 h / 20 °C

4: sodium chlorite; sodium dihydrogenphosphate / water; tert-butyl alcohol; cyclohexene / 1 h / 20 °C

5: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / dichloromethane / 14 h / Inert atmosphere

6: triphenylphosphine; di-isopropyl azodicarboxylate; trimethylsilylazide / tetrahydrofuran / 17 h / Reflux; Inert atmosphere

With 2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; copper(l) iodide; osmium(VIII) oxide; trimethylsilylazide; di-isopropyl azodicarboxylate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; triphenylphosphine; sodium iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; cyclohexene;

DOI:10.1016/j.bmc.2013.09.052

upstream raw materials:

p-toluenesulfonyl chloride