4,5,8-tris-benzyloxy-1,7-dimethoxy-3-methoxymethoxymethyl-naphthalene-2-carbaldehyde

Base Information

Chemical Name:4,5,8-tris-benzyloxy-1,7-dimethoxy-3-methoxymethoxymethyl-naphthalene-2-carbaldehyde
CAS No.:362662-55-3
Molecular Formula:C₃₇H₃₆O₈
Molecular Weight:608.688
Hs Code.:

Synonyms:4,5,8-tris-benzyloxy-1,7-dimethoxy-3-methoxymethoxymethyl-naphthalene-2-carbaldehyde

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Chemical Property of 4,5,8-tris-benzyloxy-1,7-dimethoxy-3-methoxymethoxymethyl-naphthalene-2-carbaldehyde

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Technology Process of 4,5,8-tris-benzyloxy-1,7-dimethoxy-3-methoxymethoxymethyl-naphthalene-2-carbaldehyde

There total 7 articles about 4,5,8-tris-benzyloxy-1,7-dimethoxy-3-methoxymethoxymethyl-naphthalene-2-carbaldehyde 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: 90.0%

: 362662-62-2
(4,5,8-tris-benzyloxy-1,7-dimethoxy-3-methoxymethoxymethyl-naphthalen-2-yl)-methanol

: 362662-55-3
4,5,8-tris-benzyloxy-1,7-dimethoxy-3-methoxymethoxymethyl-naphthalene-2-carbaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/ol016220e

Reference yield:

: 100-39-0
benzyl bromide

: 362662-55-3
4,5,8-tris-benzyloxy-1,7-dimethoxy-3-methoxymethoxymethyl-naphthalene-2-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / K₂CO₃; nBu₄NI / acetone / 48 h / 50 °C

2: 80 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 20 °C

3: 96 percent / NaBH₄ / tetrahydrofuran; methanol / 1.5 h / 20 °C

4: 87 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

5: 99 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

6: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; potassium carbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; acetone; 6: Dess-Martin oxidation;
DOI:10.1021/ol016220e

Reference yield:

: 362662-53-1
1,5,8-tris-benzyloxy-3-(tert-butyldimethylsiloxymethyl)-4,6-dimethoxy-naphthalene-2-carbaldehyde

: 362662-55-3
4,5,8-tris-benzyloxy-1,7-dimethoxy-3-methoxymethoxymethyl-naphthalene-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / NaBH₄ / tetrahydrofuran; methanol / 1.5 h / 20 °C

2: 87 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

3: 99 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 4: Dess-Martin oxidation;
DOI:10.1021/ol016220e