2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1357000-40-8
• Molecular Formula: C₁₆H₃₁BO₂
• Molecular Weight: 266.232
• Mol file: 1357000-40-8.mol

Synonyms:2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 12 articles about 2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 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: 93.0%

(1R,2S,5R)-menthyl chloride (16052-42-9) → 2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1357000-40-8)

Guidance literature:

With potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; at 20 ℃; for 92h; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.6b03963

Reference yield: 81.0%

(1S,2R,4R)-2-bromo-1-isopropyl-4-methylcyclohexane + bis(pinacol)diborane (73183-34-3) → 2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1357000-40-8)

Guidance literature:

With potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride; In tetrahydrofuran; at 20 ℃; for 30h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol203413w

Reference yield: 77.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (1S,2R,4R)-2-bromo-1-isopropyl-4-methylcyclohexane + benzo[1,3,2]dioxaborole (274-07-7) → 2-((1R,2R,5R)-2-isopropyl-5-methylcyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1357000-40-8)

Guidance literature:

benzo[1,3,2]dioxaborole; With bis(cyclopentadienyl)titanium dichloride; potassium carbonate; In tert-butyl methyl ether; for 0.5h;

(1S,2R,4R)-2-bromo-1-isopropyl-4-methylcyclohexane; In tert-butyl methyl ether; at 80 ℃; for 24h; under 760.051 Torr; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; With triethylamine; In tert-butyl methyl ether; at 20 ℃; for 1h; Inert atmosphere;

upstream raw materials:

(-)-menthol

(1R,2S,5R)-menthyl chloride

bis(pinacol)diborane

neomenthyl chloride

Refernces

• 1、 -. "Method for directly preparing alkyl borate compound from alkyl halide". Paragraph 0211-0213. . Retrieved 2021/04/14.
• 2、 Zhang, Li,Wu, Zhong-Qian,Jiao, Lei. "Photoinduced Radical Borylation of Alkyl Bromides Catalyzed by 4-Phenylpyridine". supporting information. p. 2095 - 2099. Retrieved 2019/12/24.