(5E)-(2R,3S)-1-benzyloxy-6-bromo-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexene

Base Information

Chemical Name:(5E)-(2R,3S)-1-benzyloxy-6-bromo-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexene
CAS No.:850699-12-6
Molecular Formula:C₂₀H₃₃BrO₂Si
Molecular Weight:413.47
Hs Code.:

Synonyms:(5E)-(2R,3S)-1-benzyloxy-6-bromo-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexene

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Chemical Property of (5E)-(2R,3S)-1-benzyloxy-6-bromo-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexene

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Technology Process of (5E)-(2R,3S)-1-benzyloxy-6-bromo-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexene

There total 6 articles about (5E)-(2R,3S)-1-benzyloxy-6-bromo-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexene 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: 99.0%

: 850699-24-0
(2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexyne

: 850699-12-6
(5E)-(2R,3S)-1-benzyloxy-6-bromo-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexene

Guidance literature:: (2S,3R)-1-benzyloxy-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexyne; With Schwartz's reagent; In dichloromethane; at 20 ℃; for 2.5h;

With N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 2.5h;
DOI:10.1021/ol050250q

Reference yield:

: 850699-11-5
(3S,4R)-5-benzyloxy-3-methyl-4-[(tert-butyldimethylsilyl)oxy]-1-pentene

: 850699-12-6
(5E)-(2R,3S)-1-benzyloxy-6-bromo-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexene

Guidance literature:: Multi-step reaction with 4 steps

1.1: 9-BBN / tetrahydrofuran / 15 h / 0 - 20 °C

1.2: 99 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 19 h / 0 - 20 °C

2.1: 94 percent / SO₃*Py; i-Pr₂NEt₂; DMSO / CH₂Cl₂ / 0.25 h / 0 °C

3.1: 88 percent / t-BuOK / tetrahydrofuran / -78 - 20 °C

4.1: ZrCp₂(H)Cl / CH₂Cl₂ / 2.5 h / 20 °C

4.2: 99 percent / N-bromosuccinimide / CH₂Cl₂ / 2.5 h / 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; Schwartz's reagent; pyridine-SO₃ complex; i-Pr₂NEt₂; potassium tert-butylate; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol050250q

Reference yield:

: 850699-23-9
(3R,4S)-5-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-3-methylpentanal

: 850699-12-6
(5E)-(2R,3S)-1-benzyloxy-6-bromo-2-[(tert-butyldimethylsilyl)oxy]-3-methyl-5-hexene

Guidance literature:: Multi-step reaction with 2 steps

1.1: 88 percent / t-BuOK / tetrahydrofuran / -78 - 20 °C

2.1: ZrCp₂(H)Cl / CH₂Cl₂ / 2.5 h / 20 °C

2.2: 99 percent / N-bromosuccinimide / CH₂Cl₂ / 2.5 h / 20 °C

With Schwartz's reagent; potassium tert-butylate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol050250q