(E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester

Base Information

Chemical Name:(E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester
CAS No.:869732-23-0
Molecular Formula:C₂₉H₃₁BrO₅
Molecular Weight:539.466
Hs Code.:

Synonyms:(E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester

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Chemical Property of (E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester

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Technology Process of (E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester

There total 6 articles about (E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester 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: 60.0%

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

: 869732-23-0
(E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 8h;
DOI:10.1021/ja055384d

Reference yield:

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

: 869732-23-0
(E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 64 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 18 h / -50 °C

2: 60 percent / triethylsilane; boron trifluoride etherate / CH₂Cl₂ / 8 h / 20 °C

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In dichloromethane;
DOI:10.1021/ja055384d

Reference yield:

: 24677-78-9
2,3-dihydroxybenzaldehyde

: 869732-23-0
(E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 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

5.1: 60 percent / triethylsilane; boron trifluoride etherate / CH₂Cl₂ / 8 h / 20 °C

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