(+)-2-[1-(tert-butyldimethylsilyloxy)-2-(3-hydroxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

Base Information

Chemical Name:(+)-2-[1-(tert-butyldimethylsilyloxy)-2-(3-hydroxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone
CAS No.:745809-37-4
Molecular Formula:C₂₉H₃₈O₈Si
Molecular Weight:542.701
Hs Code.:

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

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

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

There total 12 articles about (+)-2-[1-(tert-butyldimethylsilyloxy)-2-(3-hydroxy-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: 87.0%

: 745809-28-3
(+)-2-[1-(tert-butyldimethylsilyloxy)-2-(3-acetoxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

: 745809-37-4
(+)-2-[1-(tert-butyldimethylsilyloxy)-2-(3-hydroxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

Guidance literature:: With sodium ethanolate; In ethanol; at 0 ℃; for 2h;
DOI:10.1021/jo049426c

Reference yield:

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

: 745809-37-4
(+)-2-[1-(tert-butyldimethylsilyloxy)-2-(3-hydroxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

Guidance literature:: Multi-step reaction with 12 steps

1.1: 57 percent / sulfuric acid / 16 h

2.1: 2,6-lutidine

3.1: 92 percent / DDQ; buffer / CH₂Cl₂; H₂O / 1 h / pH 7

4.1: DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 0 °C

5.1: triphenylphosphine / CH₂Cl₂ / 0.08 h

6.1: 0.37 g / n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

7.1: 99 percent / TBAF; acetic acid / tetrahydrofuran / 2 h

8.1: 98 percent / pyridine / 18 h / 23 °C

9.1: heptane / 14 h / 57 °C

9.2: 35 percent / air / heptane; ethyl acetate / 0.25 h

10.1: 89 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.08 h

11.1: 87 percent / sodium ethoxide / ethanol / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; sulfuric acid; tetrabutyl ammonium fluoride; sodium ethanolate; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; n-heptane; dichloromethane; water; acetonitrile; 5.1: Swern oxidation / 10.1: Doetz benzannulation;
DOI:10.1021/jo049426c

Reference yield:

: 108-39-4
3-methyl-phenol

: 745809-37-4
(+)-2-[1-(tert-butyldimethylsilyloxy)-2-(3-hydroxy-5-methylphenyl)ethyl]-5,8-bis(methoxymethoxy)-[1,4]naphthoquinone

Guidance literature:: Multi-step reaction with 13 steps

1.1: 52 percent / Br₂ / acetic acid

2.1: 57 percent / sulfuric acid / 16 h

3.1: 2,6-lutidine

4.1: 92 percent / DDQ; buffer / CH₂Cl₂; H₂O / 1 h / pH 7

5.1: DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 0 °C

6.1: triphenylphosphine / CH₂Cl₂ / 0.08 h

7.1: 0.37 g / n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

8.1: 99 percent / TBAF; acetic acid / tetrahydrofuran / 2 h

9.1: 98 percent / pyridine / 18 h / 23 °C

10.1: heptane / 14 h / 57 °C

10.2: 35 percent / air / heptane; ethyl acetate / 0.25 h

11.1: 89 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.08 h

12.1: 87 percent / sodium ethoxide / ethanol / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; n-butyllithium; oxalyl dichloride; ammonium cerium(IV) nitrate; sulfuric acid; tetrabutyl ammonium fluoride; bromine; sodium ethanolate; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; n-heptane; dichloromethane; water; acetic acid; acetonitrile; 6.1: Swern oxidation / 11.1: Doetz benzannulation;
DOI:10.1021/jo049426c