methyl 2-[(2R,4S,6R)-6-(2-benzyloxyethyl)-4-bromotetrahydro-2H-pyran-2-yl]-2-methylpropanoate

Base Information

Chemical Name:methyl 2-[(2R,4S,6R)-6-(2-benzyloxyethyl)-4-bromotetrahydro-2H-pyran-2-yl]-2-methylpropanoate
CAS No.:933039-90-8
Molecular Formula:C₁₉H₂₇BrO₄
Molecular Weight:399.325
Hs Code.:

Synonyms:methyl 2-[(2R,4S,6R)-6-(2-benzyloxyethyl)-4-bromotetrahydro-2H-pyran-2-yl]-2-methylpropanoate

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Chemical Property of methyl 2-[(2R,4S,6R)-6-(2-benzyloxyethyl)-4-bromotetrahydro-2H-pyran-2-yl]-2-methylpropanoate

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Technology Process of methyl 2-[(2R,4S,6R)-6-(2-benzyloxyethyl)-4-bromotetrahydro-2H-pyran-2-yl]-2-methylpropanoate

There total 3 articles about methyl 2-[(2R,4S,6R)-6-(2-benzyloxyethyl)-4-bromotetrahydro-2H-pyran-2-yl]-2-methylpropanoate 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: 65.0%

: 933039-89-5
3-hydroxy-2,2-dimethyl-hex-5-enoic acid methyl ester

: 19790-60-4
3-Benzyloxypropanal

: 933039-90-8
methyl 2-[(2R,4S,6R)-6-(2-benzyloxyethyl)-4-bromotetrahydro-2H-pyran-2-yl]-2-methylpropanoate

Guidance literature:: With indium(III) bromide; trimethylsilyl bromide; In dichloromethane; at -78 - 25 ℃; for 16h;
DOI:10.1021/jo0624871

Reference yield:

: 13865-20-8
methyl 2,2-dimethyl-3-oxopropanoate

: 19790-60-4
3-Benzyloxypropanal

: 1730-25-2
allylmagnesium bromide

: 933039-90-8
methyl 2-[(2R,4S,6R)-6-(2-benzyloxyethyl)-4-bromotetrahydro-2H-pyran-2-yl]-2-methylpropanoate

: C₁₉H₂₇O₄Br

Guidance literature:: methyl 2,2-dimethyl-3-oxopropanoate; allylmagnesium bromide; at -78 ℃;

3-Benzyloxypropanal; With trimethylsilyl bromide; indium(III) bromide; at -78 ℃; Further stages.;
DOI:10.1039/b616558c

Reference yield:

: 14002-80-3
Methyl 2,2-dimethyl-3-hydroxypropionate

: 933039-90-8
methyl 2-[(2R,4S,6R)-6-(2-benzyloxyethyl)-4-bromotetrahydro-2H-pyran-2-yl]-2-methylpropanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 56 percent / PCC / CH₂Cl₂ / 12 h / 0 °C

2.1: (+)-DIPBr / -78 °C

2.2: TMSBr / InBr₃ / -78 °C

With pyridinium chlorochromate; In dichloromethane; 2.1: Brown allylation / 2.2: Prins cyclyzation;
DOI:10.1039/b616558c