(2S,3R,5S)-2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol

Base Information

Chemical Name:(2S,3R,5S)-2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol
CAS No.:123808-07-1
Molecular Formula:C₁₆H₂₃BrO₅
Molecular Weight:375.26
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R,5S)-2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R,5S)-2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol

There total 33 articles about (2S,3R,5S)-2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol 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: 80.0%

: 123731-62-4
(+/-)-(E)-1-(2-bromo-3,4,5-trimethoxyphenyl)-1-hepten-4-ol

: 123731-63-5,123731-70-4,123808-06-0,123808-07-1
2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol

Guidance literature:: With boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1.) 0 deg C, then rt.; 2.) 30 min, rt.;
DOI:10.1016/S0040-4020(01)80027-2

Reference yield:

: 29117-54-2
(S)-(-)-1,2-pentanediol

: 123808-07-1
(2S,3R,5S)-2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C

2: aq. ethanol / 19 h / Heating

4: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

5: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating

6: pyridine / 3 h / 0 - 5 °C

7: 88 percent / NaI, NaHCO₃ / acetone / 2 h / Heating

8: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

9: sodium acetate, bromine / 2 h / Ambient temperature

10: NaOH / methanol / 1 h / Ambient temperature

11: triethylamine / tetrahydrofuran / 2 h / 0 °C

12: DBU / benzene / 2 h / Heating

13: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature

14: 1.) m-CPBA; 2.) BF₃*Et₂O / 1.) CH₂Cl₂, 0 deg C, then rt.; 2.) 30 min, rt.

With 1H-imidazole; potassium hydroxide; sodium hydroxide; lithium borohydride; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen bromide; bromine; sodium acetate; lithium triethylborohydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4020(01)80027-2

Reference yield:

: 41014-93-1,6450-97-1
2-(S)-hydroxyvaleric acid

: 123808-07-1
(2S,3R,5S)-2-(2-bromo-3,4,5-trimethoxyphenyl)-5-propyltetrahydrofuran-3-ol

Guidance literature:: Multi-step reaction with 15 steps

1: 66 percent / LAH / diethyl ether / 1.) 0 deg C, then 3 h rt.

2: 1.) HBr; 2.) 50percent aq. KOH / 1.) AcOH, 1h; 2.) 120 deg C

3: aq. ethanol / 19 h / Heating

5: 83 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

6: 95 percent / lithium borohydride, lithium triethylborohydride / diethyl ether; tetrahydrofuran / 3 h / Heating

7: pyridine / 3 h / 0 - 5 °C

8: 88 percent / NaI, NaHCO₃ / acetone / 2 h / Heating

9: 86 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

10: sodium acetate, bromine / 2 h / Ambient temperature

11: NaOH / methanol / 1 h / Ambient temperature

12: triethylamine / tetrahydrofuran / 2 h / 0 °C

13: DBU / benzene / 2 h / Heating

14: 81 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 h / Ambient temperature

15: 1.) m-CPBA; 2.) BF₃*Et₂O / 1.) CH₂Cl₂, 0 deg C, then rt.; 2.) 30 min, rt.

With 1H-imidazole; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen bromide; bromine; sodium acetate; lithium triethylborohydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/S0040-4020(01)80027-2