3-O-(tert-butyldimethylsilyl)-5,7,3'-tri-O-(trifluoromethanesulfonyl)epicatechin

Base Information

Chemical Name:3-O-(tert-butyldimethylsilyl)-5,7,3'-tri-O-(trifluoromethanesulfonyl)epicatechin
CAS No.:299412-65-0
Molecular Formula:C₂₄H₂₅F₉O₁₂S₃Si
Molecular Weight:800.724
Hs Code.:

Synonyms:3-O-(tert-butyldimethylsilyl)-5,7,3'-tri-O-(trifluoromethanesulfonyl)epicatechin

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Chemical Property of 3-O-(tert-butyldimethylsilyl)-5,7,3'-tri-O-(trifluoromethanesulfonyl)epicatechin

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Technology Process of 3-O-(tert-butyldimethylsilyl)-5,7,3'-tri-O-(trifluoromethanesulfonyl)epicatechin

There total 3 articles about 3-O-(tert-butyldimethylsilyl)-5,7,3'-tri-O-(trifluoromethanesulfonyl)epicatechin 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:

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 299412-40-1
5,7,3',4'-tetra-O-benzyl-3-O-(tert-butyldimethylsilyl)epicatechin

: 3-O-(tert-butyldimethylsilyl)-5,7,4'-tri-O-(trifluoromethanesulfonyl)epicatechin

: 299412-65-0
3-O-(tert-butyldimethylsilyl)-5,7,3'-tri-O-(trifluoromethanesulfonyl)epicatechin

Guidance literature:: 5,7,3',4'-tetra-O-benzyl-3-O-(tert-butyldimethylsilyl)epicatechin; With hydrogen; palladium dihydroxide; In ethyl acetate; at 20 ℃; for 1h; under 750.075 Torr;

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

N,N-phenylbistrifluoromethane-sulfonimide; In N,N-dimethyl-formamide; for 2.83333h; Further stages.; cooling;
DOI:10.1021/jo000485+

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 299412-65-0
3-O-(tert-butyldimethylsilyl)-5,7,3'-tri-O-(trifluoromethanesulfonyl)epicatechin

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / imidazole / dimethylformamide / 19.5 h / 20 °C

2.1: H₂ / Pd(OH)2/C / ethyl acetate / 1 h / 20 °C / 750.08 Torr

2.2: NaH / dimethylformamide / 0.25 h / 0 °C

2.3: dimethylformamide / 2.83 h / cooling

With 1H-imidazole; hydrogen; palladium dihydroxide; In ethyl acetate; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Hydrogenolysis / 2.2: Hydrogenolysis / 2.3: Substitution;
DOI:10.1021/jo000485+

Reference yield:

: 87292-49-7
5,7,3',4'-tetra-O-benzylepicatechin

: 299412-65-0
3-O-(tert-butyldimethylsilyl)-5,7,3'-tri-O-(trifluoromethanesulfonyl)epicatechin

Guidance literature:: Multi-step reaction with 2 steps

1.1: 98 percent / imidazole / dimethylformamide / 19.5 h / 20 °C

2.1: H₂ / Pd(OH)2/C / ethyl acetate / 1 h / 20 °C / 750.08 Torr

2.2: NaH / dimethylformamide / 0.25 h / 0 °C

2.3: dimethylformamide / 2.83 h / cooling

With 1H-imidazole; hydrogen; palladium dihydroxide; In ethyl acetate; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Hydrogenolysis / 2.2: Hydrogenolysis / 2.3: Substitution;
DOI:10.1021/jo000485+