(2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan

Base Information

Chemical Name:(2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan
CAS No.:1352123-18-2
Molecular Formula:C₅₉H₅₃BrO₉
Molecular Weight:985.968
Hs Code.:

Synonyms:(2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan

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Chemical Property of (2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan

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Technology Process of (2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan

There total 5 articles about (2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan 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:

: 1352123-17-1
(2R,3S,4S)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2''-ethoxy-ethoxy)-flavan

: 135159-25-0
(2,4,6-trimethoxyphenyl)boronic acid

: 1352123-18-2
(2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan

: (2R,3S,4R)-3,5,7-Tris-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2,4,6-trimethoxy-phenyl)-chroman

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -78 - 20 ℃; for 4h; optical yield given as %de; Inert atmosphere;
DOI:10.1016/j.tet.2011.10.039

Reference yield:

: 100-44-7
benzyl chloride

: 1352123-18-2
(2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan

: (2R,3S,4R)-3,5,7-Tris-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2,4,6-trimethoxy-phenyl)-chroman

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 7.25 h / -78 - 20 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: N-Bromosuccinimide / dichloromethane / 0 - 20 °C / Inert atmosphere

3.2: 0.5 h / 0 °C / Inert atmosphere

3.3: 0 - 20 °C / Inert atmosphere

4.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 4 h / -78 - 20 °C / Inert atmosphere

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2011.10.039

Reference yield:

: 20728-73-8
5,7,3',4'-tetra-O-benzyl-(+)-catechin

: 1352123-18-2
(2R,3S,4R)-8-bromo-3,5,7,3',4'-pentabenzyloxy-4-(2'',4'',6''-trimethoxyphenyl)-flavan

: (2R,3S,4R)-3,5,7-Tris-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2,4,6-trimethoxy-phenyl)-chroman

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: N-Bromosuccinimide / dichloromethane / 0 - 20 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

2.3: 0 - 20 °C / Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran / 4 h / -78 - 20 °C / Inert atmosphere

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2011.10.039