3-(3-benzyloxymethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-hydroxy-propionic acid tert-butyl ester

Base Information

Chemical Name:3-(3-benzyloxymethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-hydroxy-propionic acid tert-butyl ester
CAS No.:364729-03-3
Molecular Formula:C₂₅H₂₆O₆
Molecular Weight:422.478
Hs Code.:

3-(3-benzyloxymethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-hydroxy-propionic acid <i>tert</i>-butyl ester

Synonyms:3-(3-benzyloxymethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-hydroxy-propionic acid tert-butyl ester

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Chemical Property of 3-(3-benzyloxymethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-hydroxy-propionic acid tert-butyl ester

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Technology Process of 3-(3-benzyloxymethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-hydroxy-propionic acid tert-butyl ester

There total 5 articles about 3-(3-benzyloxymethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-hydroxy-propionic acid tert-butyl ester 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: 97.0%

: 364729-02-2
3-(3-benzyloxymethyl-1,4-dimethoxy-naphthalen-2-yl)-3-hydroxy-propionic acid tert-butyl ester

: 364729-03-3
3-(3-benzyloxymethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-hydroxy-propionic acid tert-butyl ester

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.5h;
DOI:10.1021/ol016361g

Reference yield:

: 53772-33-1
2-bromo-3-methyl-1,4-dimethoxynaphthalene

: 364729-03-3
3-(3-benzyloxymethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-hydroxy-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / NBS; benzoyl peroxide / CCl₄ / Heating

2.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

2.2: 81 percent / tetrabutylammonium iodide / tetrahydrofuran / 8 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; various solvent(s) / 0.01 h / -95 °C

3.2: 80 percent / tetrahydrofuran; various solvent(s) / 0.67 h / -95 - 20 °C

4.1: diisopropylamine; n-BuLi / tetrahydrofuran; various solvent(s) / 0.75 h / -78 °C

4.2: 100 percent / tetrahydrofuran; various solvent(s) / 0.5 h / -78 °C

5.1: 97 percent / ammonium cerium (IV) nitrate / acetonitrile; H₂O / 0.5 h / 0 °C

With N-Bromosuccinimide; n-butyllithium; ammonium cerium(IV) nitrate; sodium hydride; diisopropylamine; dibenzoyl peroxide; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;
DOI:10.1021/ol016361g

Reference yield:

: 86489-90-9
2-bromo-3-(2-bromomethyl)-1,4-dimethoxynaphthalene

: 364729-03-3
3-(3-benzyloxymethyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl)-3-hydroxy-propionic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

1.2: 81 percent / tetrabutylammonium iodide / tetrahydrofuran / 8 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; various solvent(s) / 0.01 h / -95 °C

2.2: 80 percent / tetrahydrofuran; various solvent(s) / 0.67 h / -95 - 20 °C

3.1: diisopropylamine; n-BuLi / tetrahydrofuran; various solvent(s) / 0.75 h / -78 °C

3.2: 100 percent / tetrahydrofuran; various solvent(s) / 0.5 h / -78 °C

4.1: 97 percent / ammonium cerium (IV) nitrate / acetonitrile; H₂O / 0.5 h / 0 °C

With n-butyllithium; ammonium cerium(IV) nitrate; sodium hydride; diisopropylamine; In tetrahydrofuran; water; acetonitrile;
DOI:10.1021/ol016361g