(2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol

Base Information

Chemical Name:(2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol
CAS No.:869732-15-0
Molecular Formula:C₂₈H₃₃BrO₅
Molecular Weight:529.471
Hs Code.:

Synonyms:(2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol

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Chemical Property of (2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol

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Technology Process of (2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol

There total 7 articles about (2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol 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: 62.0%

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

: 869732-15-0
(2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol

Guidance literature:: (E)-(2S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-5-methyl-hex-3-enoic acid methyl ester; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 20 ℃; for 18h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 2.5h;
DOI:10.1021/ja055384d

Reference yield:

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

: 869732-15-0
(2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 64 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 18 h / -50 °C

2.1: 60 percent / triethylsilane; boron trifluoride etherate / CH₂Cl₂ / 8 h / 20 °C

3.1: BH₃*Me₂S / tetrahydrofuran / 18 h / 0 - 20 °C

3.2: 62 percent / H₂O₂; aq. NaOH / tetrahydrofuran; methanol / 2.5 h / 0 - 20 °C

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

Reference yield:

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

: 869732-15-0
(2R,3S,5R)-2-(benzyloxy)-6-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-5-methylhexane-1,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 60 percent / triethylsilane; boron trifluoride etherate / CH₂Cl₂ / 8 h / 20 °C

2.1: BH₃*Me₂S / tetrahydrofuran / 18 h / 0 - 20 °C

2.2: 62 percent / H₂O₂; aq. NaOH / tetrahydrofuran; methanol / 2.5 h / 0 - 20 °C

With triethylsilane; dimethylsulfide borane complex; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja055384d