(3S,4R,5R,6S)-1-bromo-3,4,5-tris[(1,1-dimethylethyl)dimethylsiloxy]-6-methoxycyclohexene

Base Information

Chemical Name:(3S,4R,5R,6S)-1-bromo-3,4,5-tris[(1,1-dimethylethyl)dimethylsiloxy]-6-methoxycyclohexene
CAS No.:372961-83-6
Molecular Formula:C₂₅H₅₃BrO₄Si₃
Molecular Weight:581.854
Hs Code.:

Synonyms:(3S,4R,5R,6S)-1-bromo-3,4,5-tris[(1,1-dimethylethyl)dimethylsiloxy]-6-methoxycyclohexene

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Chemical Property of (3S,4R,5R,6S)-1-bromo-3,4,5-tris[(1,1-dimethylethyl)dimethylsiloxy]-6-methoxycyclohexene

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Technology Process of (3S,4R,5R,6S)-1-bromo-3,4,5-tris[(1,1-dimethylethyl)dimethylsiloxy]-6-methoxycyclohexene

There total 7 articles about (3S,4R,5R,6S)-1-bromo-3,4,5-tris[(1,1-dimethylethyl)dimethylsiloxy]-6-methoxycyclohexene 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%

: 372961-82-5
(1S,4S,5R,6R)-2-bromo-4,5,6-tris[(1,1-dimethylethyl)dimethylsiloxy]-2-cyclohexen-1-ol

: 74-88-4
methyl iodide

: 372961-83-6
(3S,4R,5R,6S)-1-bromo-3,4,5-tris[(1,1-dimethylethyl)dimethylsiloxy]-6-methoxycyclohexene

Guidance literature:: With silver(l) oxide; at 110 ℃; for 24h;
DOI:10.1021/jo0159486

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 372961-83-6
(3S,4R,5R,6S)-1-bromo-3,4,5-tris[(1,1-dimethylethyl)dimethylsiloxy]-6-methoxycyclohexene

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 3.5 h / -40 °C

2: 95 percent / Ag₂O / 24 h / 110 °C

With 2,6-dimethylpyridine; silver(l) oxide; In dichloromethane;
DOI:10.1021/jo0159486

Reference yield:

: 130669-75-9
(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

: 372961-83-6
(3S,4R,5R,6S)-1-bromo-3,4,5-tris[(1,1-dimethylethyl)dimethylsiloxy]-6-methoxycyclohexene

Guidance literature:: Multi-step reaction with 5 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 15 h / 0 - 18 °C

2: 92 percent / HCl / tetrahydrofuran; H₂O / 24 h / 18 °C

3: 90 percent / AcOH; water / tetrahydrofuran / 15 h / 60 °C

4: 70 percent / 2,6-lutidine / CH₂Cl₂ / 3.5 h / -40 °C

5: 95 percent / Ag₂O / 24 h / 110 °C

With 2,6-dimethylpyridine; hydrogenchloride; water; acetic acid; 3-chloro-benzenecarboperoxoic acid; silver(l) oxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo0159486