2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-(4-phenylphenyl)menthol ester

Base Information

• Chemical Name: 2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-(4-phenylphenyl)menthol ester
• CAS No.: 732302-19-1
• Molecular Formula: C₃₄H₄₇BO₄
• Molecular Weight: 530.556
• Mol file: 732302-19-1.mol

Synonyms:

Chemical Property of 2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-(4-phenylphenyl)menthol ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-(4-phenylphenyl)menthol ester

There total 2 articles about 2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-(4-phenylphenyl)menthol ester 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:

2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (70557-99-2) + methyllithium (917-54-4) + (-)-8-(4-phenylphenyl)menthol butynoate → 2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-(4-phenylphenyl)menthol ester (732302-19-1)

Guidance literature:

methyllithium; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.166667h;

(-)-8-(4-phenylphenyl)menthol butynoate; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 2h;

DOI:10.1021/jo049773m

Reference yield:

(-)-8-(4-phenylphenyl)menthol (322640-14-2) → 2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-(4-phenylphenyl)menthol ester (732302-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 24 percent / 4-dimethylaminopyridine; DCC / CH₂Cl₂ / 20 °C

2.1: CuBr*SMe₂ / diethyl ether; tetrahydrofuran / 0.17 h / 0 °C

2.2: diethyl ether; tetrahydrofuran / 1 h / -78 °C

2.3: HMPA / tetrahydrofuran; diethyl ether / 2 h / -78 - 20 °C

With dmap; copper(I) bromide dimethylsulfide complex; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo049773m

Reference yield:

3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) + 2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-(4-phenylphenyl)menthol ester (732302-19-1) → (S)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4,4-dimethyl-3-methylenedihydrofuran-2-one + (R)-5-(2-(tert-butyldiphenylsilyloxy)ethyl)-4,4-dimethyl-3-methylenedihydrofuran-2-one

Guidance literature:

3-(tert-butyldiphenylsilyloxy)-1-propanal; 2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-(4-phenylphenyl)menthol ester; In toluene; at 20 ℃; for 576h;

With toluene-4-sulfonic acid; In toluene; at 20 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1021/jo049773m

upstream raw materials:

2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

methyllithium

(-)-8-(4-phenylphenyl)menthol

Refernces