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

Base Information

Chemical Name:methyl (2S,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-carboxylate
CAS No.:924268-12-2
Molecular Formula:C₁₈H₂₅BrO₇
Molecular Weight:433.296
Hs Code.:

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

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Chemical Property of methyl (2S,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-carboxylate

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Technology Process of methyl (2S,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-carboxylate

There total 4 articles about methyl (2S,3S,5S,6S)-6-(3-bromo-2,5,6-trimethoxyphenyl)-3-methoxy-5-methyl-tetrahydro-2H-pyran-2-carboxylate 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: 97.0%

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

: 420-37-1
trimethoxonium tetrafluoroborate

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

Guidance literature:: With Proton Sponge; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/ja067234o

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

With Proton Sponge; trifluorormethanesulfonic acid; dimethylsulfide borane complex; 4 A molecular sieve; In tetrahydrofuran; 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

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

Guidance literature:: Multi-step reaction with 2 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

With Proton Sponge; dimethylsulfide borane complex; 4 A molecular sieve; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja067234o