(2S,4R,6S)-2-(3'',4''-dihydroxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate

Base Information

Chemical Name:(2S,4R,6S)-2-(3'',4''-dihydroxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate
CAS No.:1440432-12-1
Molecular Formula:C₃₁H₃₅BrO₉
Molecular Weight:631.517
Hs Code.:

(2S,4R,6S)-2-(3'',4''-dihydroxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate

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Chemical Property of (2S,4R,6S)-2-(3'',4''-dihydroxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate

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Technology Process of (2S,4R,6S)-2-(3'',4''-dihydroxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate

There total 3 articles about (2S,4R,6S)-2-(3'',4''-dihydroxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate 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:

: 75-44-5
phosgene

: 2973-76-4
5-bromo-4-hydroxy-3-methoxybenzaldehyde

: 5406-18-8
3-(p-methoxyphenyl)-1-propanol

: 1440432-71-2
(S)-1-(3′,4′-dibenzyloxyphenyl)hex-5-ene-3-ol

: 1440432-12-1
(2S,4R,6S)-2-(3'',4''-dihydroxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate

Guidance literature:: 5-bromo-4-hydroxy-3-methoxybenzaldehyde; With tetra-(n-butyl)ammonium iodide; caesium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 16h; Inert atmosphere;

(S)-1-(3′,4′-dibenzyloxyphenyl)hex-5-ene-3-ol; With trimethylsilyl acetate; acetic acid; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

phosgene; 3-(p-methoxyphenyl)-1-propanol; Further stages;
DOI:10.1002/anie.201205728

Reference yield:

: 524004-38-4
3-[3,4-bis(benzyloxy)phenyl]propan-1-ol

: 1440432-12-1
(2S,4R,6S)-2-(3'',4''-dihydroxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hydrogencarbonate; sodium hypochlorite / dichloromethane; water / -10 - 5 °C

2.1: B-chlorodiisopinocampheylborane / tetrahydrofuran / 2.5 h / -75 - 20 °C

2.2: 2.5 h / -100 - 20 °C

3.1: caesium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere

3.2: 0.17 h / 20 °C

With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; caesium carbonate; B-chlorodiisopinocampheylborane; potassium bromide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/anie.201205728

Reference yield:

: 95301-39-6
3-(3',4'-dibenzyloxyphenyl)propanal

: 1440432-12-1
(2S,4R,6S)-2-(3'',4''-dihydroxyphenethyl)-6-(3'''-bromo-4'''-hydroxy-5'''-methoxyphenyl)tetrahydropyran-4-yl-3''''-(4'''''-methoxyphenyl)propyl carbonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: B-chlorodiisopinocampheylborane / tetrahydrofuran / 2.5 h / -75 - 20 °C

1.2: 2.5 h / -100 - 20 °C

2.1: caesium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere

2.2: 0.17 h / 20 °C

With tetra-(n-butyl)ammonium iodide; caesium carbonate; B-chlorodiisopinocampheylborane; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1002/anie.201205728