(2S,5S,6R,E)-methyl 2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-hydroxy-5-methylhex-3-enoate

Base Information

Chemical Name:(2S,5S,6R,E)-methyl 2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-hydroxy-5-methylhex-3-enoate
CAS No.:869732-14-9
Molecular Formula:C₂₉H₃₁BrO₆
Molecular Weight:555.466
Hs Code.:

Synonyms:(2S,5S,6R,E)-methyl 2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-hydroxy-5-methylhex-3-enoate

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Chemical Property of (2S,5S,6R,E)-methyl 2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-hydroxy-5-methylhex-3-enoate

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Technology Process of (2S,5S,6R,E)-methyl 2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-hydroxy-5-methylhex-3-enoate

There total 5 articles about (2S,5S,6R,E)-methyl 2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-hydroxy-5-methylhex-3-enoate 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: 64.0%

: 869732-13-8
3-(benzyloxy)-5-bromo-2-methoxybenzaldehyde

: (2R,3R,E)-methyl 2-(benzyloxy)-3-(dimethyl(phenyl)silyl)hex-4-enoate

: 869732-14-9
(2S,5S,6R,E)-methyl 2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-hydroxy-5-methylhex-3-enoate

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -50 ℃; for 18h;
DOI:10.1021/ja055384d

Reference yield:

: 24677-78-9
2,3-dihydroxybenzaldehyde

: 869732-14-9
(2S,5S,6R,E)-methyl 2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-hydroxy-5-methylhex-3-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 73 percent / tetrahydrofuran / 24 h

2.1: Br₂; AcOH; AcONa / 0.5 h

3.1: 16.4 g / K₂CO₃ / dimethylformamide / 24 h / 20 °C

4.1: 64 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 18 h / -50 °C

With trimethylsilyl trifluoromethanesulfonate; bromine; sodium acetate; sodium hydride; potassium carbonate; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja055384d

Reference yield:

: 100-39-0
benzyl bromide

: 869732-14-9
(2S,5S,6R,E)-methyl 2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-6-hydroxy-5-methylhex-3-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 73 percent / tetrahydrofuran / 24 h

2.1: Br₂; AcOH; AcONa / 0.5 h

3.1: 16.4 g / K₂CO₃ / dimethylformamide / 24 h / 20 °C

4.1: 64 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 18 h / -50 °C

With trimethylsilyl trifluoromethanesulfonate; bromine; sodium acetate; sodium hydride; potassium carbonate; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja055384d