2-[2-(tert-butyldimethylsilanyloxy)-2-(3-acetoxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

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Chemical Name:2-[2-(tert-butyldimethylsilanyloxy)-2-(3-acetoxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone
CAS No.:745809-58-9
Molecular Formula:C₃₁H₄₀O₉Si
Molecular Weight:584.739
Hs Code.:

Synonyms:2-[2-(tert-butyldimethylsilanyloxy)-2-(3-acetoxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

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Chemical Property of 2-[2-(tert-butyldimethylsilanyloxy)-2-(3-acetoxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

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Technology Process of 2-[2-(tert-butyldimethylsilanyloxy)-2-(3-acetoxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

There total 10 articles about 2-[2-(tert-butyldimethylsilanyloxy)-2-(3-acetoxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone 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: 84.0%

: 745809-51-2
acetic acid 3-[1-(tert-butyl-dimethyl-silanyloxy)-2-(1-hydroxy-4-methoxy-5,8-bis-methoxymethoxy-naphthalen-2-yl)-ethyl]-5-methyl-phenyl ester

: 745809-58-9
2-[2-(tert-butyldimethylsilanyloxy)-2-(3-acetoxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; for 0.0833333h;
DOI:10.1021/jo049426c

Reference yield:

: 58169-99-6
2,3,4,6-tetrabromo-5-methyl-phenol

: 745809-58-9
2-[2-(tert-butyldimethylsilanyloxy)-2-(3-acetoxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

Guidance literature:: Multi-step reaction with 8 steps

1.1: HI / H₂O / Heating

1.2: 2,6-lutidine

2.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C

2.2: 95 percent / tetrahydrofuran; pentane / 0.5 h / 0 °C

3.1: n-BuLi; TMEDA / diethyl ether; hexane; toluene / 0.03 h / -78 °C

3.2: 68 percent / various solvents / 1 h / -78 - 23 °C

4.1: 68 percent / imidazole; DMAP / CH₂Cl₂ / 16 h / 23 °C

5.1: TBAF; HOAc / tetrahydrofuran / 0 - 23 °C

6.1: 148 mg / pyridine / 16 h

7.1: tetrahydrofuran / 14 h / 54 °C

7.2: 36 percent / air / tetrahydrofuran; diethyl ether / 0.25 h

8.1: 84 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.08 h

With pyridine; 1H-imidazole; dmap; n-butyllithium; ammonium cerium(IV) nitrate; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; hydrogen iodide; tert.-butyl lithium; acetic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; pentane; 7.1: Doetz benzannulation;
DOI:10.1021/jo049426c

Reference yield:

: 34946-83-3
2,4,4,6-tetrabromo-3-methyl-cyclohexa-2,5-dienone

: 745809-58-9
2-[2-(tert-butyldimethylsilanyloxy)-2-(3-acetoxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 57 percent / sulfuric acid / 16 h

2.1: HI / H₂O / Heating

2.2: 2,6-lutidine

3.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C

3.2: 95 percent / tetrahydrofuran; pentane / 0.5 h / 0 °C

4.1: n-BuLi; TMEDA / diethyl ether; hexane; toluene / 0.03 h / -78 °C

4.2: 68 percent / various solvents / 1 h / -78 - 23 °C

5.1: 68 percent / imidazole; DMAP / CH₂Cl₂ / 16 h / 23 °C

6.1: TBAF; HOAc / tetrahydrofuran / 0 - 23 °C

7.1: 148 mg / pyridine / 16 h

8.1: tetrahydrofuran / 14 h / 54 °C

8.2: 36 percent / air / tetrahydrofuran; diethyl ether / 0.25 h

9.1: 84 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.08 h

With pyridine; 1H-imidazole; dmap; n-butyllithium; ammonium cerium(IV) nitrate; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen iodide; tert.-butyl lithium; acetic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; pentane; 8.1: Doetz benzannulation;
DOI:10.1021/jo049426c