(3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Base Information

Chemical Name:(3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane
CAS No.:387834-42-6
Molecular Formula:C₂₅H₅₁BO₄Si₂
Molecular Weight:482.66
Hs Code.:

Synonyms:(3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

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Chemical Property of (3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

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Technology Process of (3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

There total 4 articles about (3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-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: 90.0%

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 387834-41-5
(3R,5R)-1-bromomethylene-3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexane

: 387834-42-6
(3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Guidance literature:: (3R,5R)-1-bromomethylene-3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 1h;

With Triisopropyl borate; In diethyl ether; pentane; at -78 - 20 ℃;

2,3-dimethyl-2,3-butane diol; With magnesium sulfate; In ethyl acetate; at 20 ℃; for 24h; Further stages.;
DOI:10.1021/ol016908r

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 387834-42-6
(3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

2.2: B(O-i-Pr)3 / diethyl ether; pentane / -78 - 20 °C

2.3: 90 percent / MgSO₄ / ethyl acetate / 24 h / 20 °C

With 1H-imidazole; tert.-butyl lithium; In diethyl ether; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol016908r

Reference yield:

: 387834-43-7
(1R,4R,6S)-(E)-2-bromomethylene-4-(tert-butyldimethylsilyloxy)-7-oxa-bicyclo[4.1.0]heptane

: 387834-42-6
(3R,5R)-2-[3,5-bis-(tert-butyldimethylsilanyloxy)cyclohexylidenemethyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 82 percent / i-Bu₂AlH / hexane / 1.5 h / 0 °C

2.1: 93 percent / imidazole / dimethylformamide / 12 h / 20 °C

3.1: t-BuLi / diethyl ether; pentane / 1 h / -78 °C

3.2: B(O-i-Pr)3 / diethyl ether; pentane / -78 - 20 °C

3.3: 90 percent / MgSO₄ / ethyl acetate / 24 h / 20 °C

With 1H-imidazole; tert.-butyl lithium; diisobutylaluminium hydride; In diethyl ether; hexane; N,N-dimethyl-formamide; pentane;
DOI:10.1021/ol016908r