(2R,3S)-2-(benzyloxy)methyl-1-bromo-3-(tert-butyldimethylsilyloxy)hex-5-en-1-yne

Base Information

Chemical Name:(2R,3S)-2-(benzyloxy)methyl-1-bromo-3-(tert-butyldimethylsilyloxy)hex-5-en-1-yne
CAS No.:1268600-41-4
Molecular Formula:C₂₀H₂₉BrO₂Si
Molecular Weight:409.439
Hs Code.:

Synonyms:(2R,3S)-2-(benzyloxy)methyl-1-bromo-3-(tert-butyldimethylsilyloxy)hex-5-en-1-yne

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Chemical Property of (2R,3S)-2-(benzyloxy)methyl-1-bromo-3-(tert-butyldimethylsilyloxy)hex-5-en-1-yne

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Technology Process of (2R,3S)-2-(benzyloxy)methyl-1-bromo-3-(tert-butyldimethylsilyloxy)hex-5-en-1-yne

There total 3 articles about (2R,3S)-2-(benzyloxy)methyl-1-bromo-3-(tert-butyldimethylsilyloxy)hex-5-en-1-yne 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: 92.0%

: 42867-45-8
(dibromomethylene)triphenylphosphorane

: 1268600-40-3
(2R,3S)-2-(benzyloxy)methyl-3-(tert-butyldimethylsilybutyldimethylsilyloxy)pent-4-en-al

: 1268600-41-4
(2R,3S)-2-(benzyloxy)methyl-1-bromo-3-(tert-butyldimethylsilyloxy)hex-5-en-1-yne

Guidance literature:: (dibromomethylene)triphenylphosphorane; With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.0833333h; Inert atmosphere;

(2R,3S)-2-(benzyloxy)methyl-3-(tert-butyldimethylsilybutyldimethylsilyloxy)pent-4-en-al; With potassium tert-butylate; In tetrahydrofuran; at -78 - 0 ℃; for 0.566667h; Inert atmosphere;
DOI:10.1021/jo2000308

Reference yield:

: 1268600-51-6
(4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

: 1268600-41-4
(2R,3S)-2-(benzyloxy)methyl-1-bromo-3-(tert-butyldimethylsilyloxy)hex-5-en-1-yne

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.22 h / -78 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere

2.2: 0.57 h / -78 - 0 °C / Inert atmosphere

With potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo2000308

Reference yield:

: (4S)-3-[(2R,3S)-3-hydroxy-2-[(benzyloxy)methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

: 1268600-41-4
(2R,3S)-2-(benzyloxy)methyl-1-bromo-3-(tert-butyldimethylsilyloxy)hex-5-en-1-yne

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.83 h / 0 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.22 h / -78 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere

3.2: 0.57 h / -78 - 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo2000308