(2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylepicatechin

Base Information

Chemical Name:(2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylepicatechin
CAS No.:1390643-85-2
Molecular Formula:C₄₂H₄₆O₆Si
Molecular Weight:674.909
Hs Code.:

Synonyms:(2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylepicatechin

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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 (2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylepicatechin

Chemical Property:

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Technology Process of (2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylepicatechin

There total 12 articles about (2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylepicatechin 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: 73.0%

: 1390643-82-9
(2R)-4'-(tert-butyldimethylsilyloxy)-5,7,3'-tribenzyloxyflavan-3-one

: 1390643-85-2
(2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylepicatechin

Guidance literature:: With L-Selectride; In tetrahydrofuran; at -78 ℃; for 8h; enantioselective reaction; Inert atmosphere;
DOI:10.1021/ol3016463

Reference yield:

: 889471-78-7
(E)-2-(benzyloxy)-4-(3-hydroxyprop-1-en-1-yl)phenol

: 1390643-85-2
(2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylepicatechin

Guidance literature:: Multi-step reaction with 9 steps

1.1: Montmorillonite K-10 clay / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

1.2: 13.5 h / 20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere

3.1: AD-mix-α; methanesulfonamide / dichloromethane; water; tert-butyl alcohol / 72 h / 0 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 5.3 h / 20 - 55 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere

8.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

9.1: L-Selectride / tetrahydrofuran / 8 h / -78 °C / Inert atmosphere

With methanesulfonamide; AD-mix-α; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; L-Selectride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; 1.1: Friedel Crafts alkylation / 1.2: Friedel Crafts alkylation;
DOI:10.1021/ol3016463

Reference yield:

: 1390643-79-4
(2R,3S)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylcatechin

: 1390643-85-2
(2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzylepicatechin

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: L-Selectride / tetrahydrofuran / 8 h / -78 °C / Inert atmosphere

With L-Selectride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol3016463