(1R,2R,4S,5S)-4,5-dicyclohexyl-2-[2-azido-1-bromo-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-1,3,2-dioxaborolane

Base Information

Chemical Name:(1R,2R,4S,5S)-4,5-dicyclohexyl-2-[2-azido-1-bromo-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-1,3,2-dioxaborolane
CAS No.:304915-09-1
Molecular Formula:C₂₃H₄₃BBrN₃O₃Si
Molecular Weight:528.413
Hs Code.:

Synonyms:(1R,2R,4S,5S)-4,5-dicyclohexyl-2-[2-azido-1-bromo-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-1,3,2-dioxaborolane

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Chemical Property of (1R,2R,4S,5S)-4,5-dicyclohexyl-2-[2-azido-1-bromo-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-1,3,2-dioxaborolane

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Technology Process of (1R,2R,4S,5S)-4,5-dicyclohexyl-2-[2-azido-1-bromo-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-1,3,2-dioxaborolane

There total 6 articles about (1R,2R,4S,5S)-4,5-dicyclohexyl-2-[2-azido-1-bromo-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-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: 95.0%

: 304915-08-0
[2(1S),4S,5S]-4,5-dicyclohexyl-2-[1-azido-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane

: 74-95-3
1,1-dibromomethane

: 304915-09-1
(1R,2R,4S,5S)-4,5-dicyclohexyl-2-[2-azido-1-bromo-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-1,3,2-dioxaborolane

Guidance literature:: [2(1S),4S,5S]-4,5-dicyclohexyl-2-[1-azido-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane; 1,1-dibromomethane; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃;

With zinc(II) chloride; In tetrahydrofuran; hexane; at -78 - 25 ℃; for 24h; Further stages.;
DOI:10.1021/jo005522b

Reference yield:

: 304915-04-6
(4S,5S)-4,5-dicyclohexyl-2-(benzyloxy)methyl-1,3,2-dioxaborolane

: 304915-09-1
(1R,2R,4S,5S)-4,5-dicyclohexyl-2-[2-azido-1-bromo-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-1,3,2-dioxaborolane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / H₂ / Pd/C / ethyl acetate / 24 h / 20 - 25 °C / 760.05 Torr

2.1: 82 percent / imidazole / ethyl acetate / 24 h / 20 - 25 °C

3.1: tetrahydrofuran / -100 °C

3.2: 97 percent / ZnCl₂ / tetrahydrofuran / -100 - 25 °C

4.1: 98 percent / sodium azide; tetrabutylammonium bromide / H₂O; nitromethane / 240 h / 20 - 25 °C

5.1: LDA / hexane; tetrahydrofuran / -78 °C

5.2: 95 percent / ZnCl₂ / hexane; tetrahydrofuran / 24 h / -78 - 25 °C

With 1H-imidazole; sodium azide; tetrabutylammomium bromide; hydrogen; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; nitromethane; hexane; water; ethyl acetate; 1.1: Hydrogenolysis / 2.1: silylation / 3.1: Addition / 3.2: Rearrangement / 4.1: Substitution / 5.1: Addition / 5.2: Rearrangement;
DOI:10.1021/jo005522b

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 304915-09-1
(1R,2R,4S,5S)-4,5-dicyclohexyl-2-[2-azido-1-bromo-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]-1,3,2-dioxaborolane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 82 percent / imidazole / ethyl acetate / 24 h / 20 - 25 °C

2.1: tetrahydrofuran / -100 °C

2.2: 97 percent / ZnCl₂ / tetrahydrofuran / -100 - 25 °C

3.1: 98 percent / sodium azide; tetrabutylammonium bromide / H₂O; nitromethane / 240 h / 20 - 25 °C

4.1: LDA / hexane; tetrahydrofuran / -78 °C

4.2: 95 percent / ZnCl₂ / hexane; tetrahydrofuran / 24 h / -78 - 25 °C

With 1H-imidazole; sodium azide; tetrabutylammomium bromide; lithium diisopropyl amide; In tetrahydrofuran; nitromethane; hexane; water; ethyl acetate; 1.1: silylation / 2.1: Addition / 2.2: Rearrangement / 3.1: Substitution / 4.1: Addition / 4.2: Rearrangement;
DOI:10.1021/jo005522b