6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3-hydroxy-3-(hydroxymethyl)benzofuran-4-yl 4-methylbenzenesulfonate

Base Information

• Chemical Name: 6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3-hydroxy-3-(hydroxymethyl)benzofuran-4-yl 4-methylbenzenesulfonate
• CAS No.: 1312466-21-9
• Molecular Formula: C₃₂H₃₁BrO₉S
• Molecular Weight: 671.563
• Mol file: 1312466-21-9.mol

Synonyms:6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3-hydroxy-3-(hydroxymethyl)benzofuran-4-yl 4-methylbenzenesulfonate

Chemical Property of 6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3-hydroxy-3-(hydroxymethyl)benzofuran-4-yl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3-hydroxy-3-(hydroxymethyl)benzofuran-4-yl 4-methylbenzenesulfonate

There total 11 articles about 6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3-hydroxy-3-(hydroxymethyl)benzofuran-4-yl 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: 85.0%

3-(ethoxycarbonyl)-6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3-hydroxybenzofuran-4-yl 4-methylbenzenesulfonate (1312466-20-8) → 6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3-hydroxy-3-(hydroxymethyl)benzofuran-4-yl 4-methylbenzenesulfonate (1312466-21-9)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/ol201332u

Reference yield:

2-bromo-4-hydroxybenzaldehyde (22532-60-1) → 6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3-hydroxy-3-(hydroxymethyl)benzofuran-4-yl 4-methylbenzenesulfonate (1312466-21-9)

Guidance literature:

Multi-step reaction with 7 steps

1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 70 °C

2: tetrahydrofuran; ethanol / 6 h / 0 °C / Reflux

3: magnesium bromide / diethyl ether / 2 h / 20 °C

4: 6-chloro-5-phenylpyrimidine-4-(9-O-quinidine) ether; tetra-(n-butyl)ammonium iodide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / tetrahydrofuran / 0.5 h / -78 °C

5: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C

6: triethylamine / dichloromethane / 3 h / 20 °C

7: lithium borohydride / tetrahydrofuran / 0 - 20 °C

With lithium borohydride; 6-chloro-5-phenylpyrimidine-4-(9-O-quinidine) ether; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; triethylamine; magnesium bromide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 2: Darzens condensation / 4: Feist-Benary interrupted synthesis;

DOI:10.1021/ol201332u

Reference yield:

ethyl 3-bromo-3-(4-benzyloxy-2-bromophenyl)-2-oxopropanoate (1338067-80-3) → 6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3-hydroxy-3-(hydroxymethyl)benzofuran-4-yl 4-methylbenzenesulfonate (1312466-21-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 6-chloro-5-phenylpyrimidine-4-(9-O-quinidine) ether; tetra-(n-butyl)ammonium iodide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / tetrahydrofuran / 0.5 h / -78 °C

2: potassium tert-butylate / tetrahydrofuran / 2 h / 0 °C

3: triethylamine / dichloromethane / 3 h / 20 °C

4: lithium borohydride / tetrahydrofuran / 0 - 20 °C

With lithium borohydride; 6-chloro-5-phenylpyrimidine-4-(9-O-quinidine) ether; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; triethylamine; In tetrahydrofuran; dichloromethane; 1: Feist-Benary interrupted synthesis;

DOI:10.1021/ol201332u

upstream raw materials:

ethyl 3-(4-benzyloxy-2-bromophenyl)-2-ethoxyoxirane-2-carboxylate

ethyl 3-bromo-3-(4-benzyloxy-2-bromophenyl)-2-oxopropanoate

C₂₇H₂₇BrO₈

ethyl 6-(3-hydroxypropoxy)-2-(4-(benzyloxy)-2-bromophenyl)-2,3-dihydro-3,4-dihydroxybenzofuran-3-carboxylate

Downstream raw materials:

9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6a-hydroxy-6H-benzofuro[3,2-c]chromen-7-yl 4-methylbenzenesulfonate

9-(3-hydroxypropoxy)-3-(benzyloxy)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a-ol

3-benzyloxy-6a,11a-dihydro-6H-benzofuro[3,2-c]chromen-6a,9-diol