[(2R,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-yl]methanol

Base Information

Chemical Name:[(2R,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-yl]methanol
CAS No.:924268-17-7
Molecular Formula:C₁₇H₂₅BrO₆
Molecular Weight:405.286
Hs Code.:

Synonyms:[(2R,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-yl]methanol

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Chemical Property of [(2R,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-yl]methanol

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Technology Process of [(2R,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-yl]methanol

There total 5 articles about [(2R,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-yl]methanol 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: 98.0%

: 924268-12-2
methyl (2S,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-carboxylate

: 924268-17-7
[(2R,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-yl]methanol

Guidance literature:: With lithium borohydride; In methanol; diethyl ether; at 0 - 20 ℃;
DOI:10.1021/ja067234o

Reference yield:

: 3-bromo-2,5,6-trimethoxybenzaldehyde

: 924268-17-7
[(2R,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-yl]methanol

Guidance literature:: Multi-step reaction with 4 steps

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

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

2.2: 79 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 1.5 h / 0 - 20 °C

3.1: 97 percent / proton sponge; molecular sieves 4 Angstroem / CH₂Cl₂ / 12 h / 20 °C

4.1: 98 percent / LiBH₄ / diethyl ether; methanol / 0 - 20 °C

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

Reference yield:

: methyl (2S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-5-methyl-5,6-dihydro-2H-pyran-2-carboxylate

: 924268-17-7
[(2R,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-yl]methanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: BH₃*Me₂S / tetrahydrofuran / 0 - 20 °C

1.2: 79 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 1.5 h / 0 - 20 °C

2.1: 97 percent / proton sponge; molecular sieves 4 Angstroem / CH₂Cl₂ / 12 h / 20 °C

3.1: 98 percent / LiBH₄ / diethyl ether; methanol / 0 - 20 °C

With lithium borohydride; Proton Sponge; dimethylsulfide borane complex; 4 A molecular sieve; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja067234o