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

Base Information

Chemical Name:(2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzyl-3-acetylepicatechin
CAS No.:1390643-88-5
Molecular Formula:C₄₄H₄₈O₇Si
Molecular Weight:716.946
Hs Code.:

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

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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-benzyl-3-acetylepicatechin

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

There total 13 articles about (2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzyl-3-acetylepicatechin 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: 79.0%

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

: 75-36-5
acetyl chloride

: 1390643-88-5
(2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzyl-3-acetylepicatechin

Guidance literature:: With pyridine; dmap; In dichloromethane; at 0 - 20 ℃; for 2.5h; Inert atmosphere;
DOI:10.1021/ol3016463

Reference yield:

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

: 1390643-88-5
(2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzyl-3-acetylepicatechin

Guidance literature:: Multi-step reaction with 10 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

10.1: pyridine; dmap / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; 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

: 1390643-88-5
(2R,3R)-4'-(tert-butyldimethylsilyl)-5,7,3'-tri-O-benzyl-3-acetylepicatechin

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: pyridine; dmap / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere

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