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

Base Information

Chemical Name:2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-phenylmenthol ester
CAS No.:403806-07-5
Molecular Formula:C₂₈H₄₃BO₄
Molecular Weight:454.458
Hs Code.:

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

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

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Technology Process of 2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-phenylmenthol 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-phenylmenthol 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: 44.0%

: 70557-99-2
2-(iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 917-54-4
methyllithium

: 169136-81-6
(-)-(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl tetrolate

: 403806-07-5
2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-phenylmenthol ester

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

(-)-(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl tetrolate; 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:

: 65253-04-5
(-)-8-phenylmenthol

: 403806-07-5
2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-phenylmenthol ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 89 percent / 4-dimethylaminopyridine; DCC / CH₂Cl₂ / -78 - 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: 44 percent / 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:

: 112897-03-7
3-(tert-butyldiphenylsilyloxy)-1-propanal

: 403806-07-5
2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-3-methylbut-2-enoic acid (-)-8-phenylmenthol ester

: (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-phenylmenthol ester; In toluene; at 20 ℃; for 864h;

With toluene-4-sulfonic acid; In toluene; at 20 ℃; for 0.5h; Title compound not separated from byproducts;
DOI:10.1021/jo049773m