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

Base Information

Chemical Name:(2R,3S,5R)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol
CAS No.:869732-27-4
Molecular Formula:C₂₂H₂₉BrO₅
Molecular Weight:453.373
Hs Code.:

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

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

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

There total 16 articles about (2R,3S,5R)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-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: 90.0%

: 869732-26-3
(2R,3S,5R)-2-Benzyloxy-6-(3-benzyloxy-5-bromo-2-methoxy-phenyl)-3-methoxy-5-methyl-hexan-1-ol

: 869732-27-4
(2R,3S,5R)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol

Guidance literature:: With boron trichloride - methyl sulfide complex; In dichloromethane; at -78 - 0 ℃; for 5h;
DOI:10.1021/ja055384d

Reference yield: 63.0%

: 924268-57-5
[(2R,3S,5S,6S)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-3-methoxy-5-methyl-5,6-tetrahydro-2H-pyran-2-yl]methanol

: 869732-27-4
(2R,3S,5R)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol

Guidance literature:: With triethylsilane; scandium tris(trifluoromethanesulfonate); In dichloromethane; at 25 ℃; for 24h;
DOI:10.1021/ja067234o

Reference yield:

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

: 869732-27-4
(2R,3S,5R)-6-(3-benzyloxy-5-bromo-2-methoxyphenyl)-3-methoxy-5-methylhexane-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 87 percent / triflic acid / CH₂Cl₂ / 24 h / -78 °C

2.1: BH₃*Me₂S / tetrahydrofuran / 8 h / 20 °C

2.2: aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.1: proton sponge; molecular sieves 4 Angstroem / CH₂Cl₂ / 12 h / 20 °C

4.1: 126.3 mg / LiBH₄ / diethyl ether; methanol / 0 - 20 °C

5.1: 63 percent / Et₃SiH; Sc(OTf)3 / CH₂Cl₂ / 24 h / 25 °C

With triethylsilane; lithium borohydride; Proton Sponge; trifluorormethanesulfonic acid; dimethylsulfide borane complex; 4 A molecular sieve; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja067234o