1,3,6,8-tetramethoxy-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-anthraquinone

Base Information

Chemical Name:1,3,6,8-tetramethoxy-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-anthraquinone
CAS No.:914933-69-0
Molecular Formula:C₃₃H₄₆O₉Si
Molecular Weight:614.808
Hs Code.:

Synonyms:1,3,6,8-tetramethoxy-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-anthraquinone

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Chemical Property of 1,3,6,8-tetramethoxy-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-anthraquinone

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Technology Process of 1,3,6,8-tetramethoxy-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-anthraquinone

There total 2 articles about 1,3,6,8-tetramethoxy-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-anthraquinone 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: 17.0%

: 914933-62-3
2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-benzaldehyde

: 142601-55-6
N,N-diethyl-2,4-dimethoxybenzamide

: 914933-69-0
1,3,6,8-tetramethoxy-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-anthraquinone

: 2-({3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-phenyl}-hydroxy-methyl)-N,N-diethyl-4,6-dimethoxy-benzamide

Guidance literature:: 2-bromo-3,5-dimethoxy-4-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-benzaldehyde; N,N-diethyl-2,4-dimethoxybenzamide; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - 20 ℃;
DOI:10.1021/ol0617291

Reference yield:

: 56518-42-4
4-bromo-3,5-dimethoxybenzoic acid

: 914933-69-0
1,3,6,8-tetramethoxy-2-[2-(2-methyl-[1,3]dioxolan-2-yl)-1-triisopropylsilanyloxy-ethyl]-anthraquinone

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / BH₃*SMe₂ / tetrahydrofuran / 40 °C

2.1: 100 percent / imidazole; 4-DMAP / CH₂Cl₂ / 20 °C

3.1: 67 percent / t-BuLi / pentane; tetrahydrofuran / -78 - 20 °C

4.1: 94 percent / imidazole; 4-DMAP / dimethylformamide / 20 °C

5.1: 100 percent / NBS / acetonitrile / 1.5 h / 20 °C

6.1: 100 percent / TBAF / tetrahydrofuran / 0.33 h / 20 °C

7.1: 81 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 °C

8.1: sec-BuLi; TMEDA / tetrahydrofuran / 1 h / -78 °C

8.2: 17 percent / tert-BuLi / tetrahydrofuran; pentane / -78 - 20 °C

With 1H-imidazole; dmap; N-Bromosuccinimide; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; tert.-butyl lithium; sec.-butyllithium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; pentane; 7.1: Swern oxidation;
DOI:10.1021/ol0617291