(3aS,4R,9aS)-3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one

Base Information

Chemical Name:(3aS,4R,9aS)-3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one
CAS No.:1002342-05-3
Molecular Formula:C₂₀H₂₀O₆
Molecular Weight:356.375
Hs Code.:

Synonyms:(3aS,4R,9aS)-3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one

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Chemical Property of (3aS,4R,9aS)-3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one

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Technology Process of (3aS,4R,9aS)-3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one

There total 10 articles about (3aS,4R,9aS)-3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one 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: 76.0%

: (3aS,4R,9aS)-6-benzyloxy-4-(4-benzyloxy-3-methoxyphenyl)-3a,4,9,9a-tetrahydro-7-methoxynaphtho[2,3-c]furan-1(3H)-one

: 1002342-05-3
(3aS,4R,9aS)-3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one

Guidance literature:: With 5%-palladium/activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 5h;
DOI:10.1080/09168451.2020.1777081

Reference yield:

: (2S,3S,4R)-[6-benzyloxy-4-(4-benzyloxy-3-methoxyphenyl)-1,2,3,4-tetrahydro-3-hydroxymethyl-7-methoxy-2-naphthyl]methyl pivaloate

: 1002342-05-3
(3aS,4R,9aS)-3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one

Guidance literature:: Multi-step reaction with 7 steps

1: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C

2: diisobutylaluminium hydride / toluene / 1 h / -10 °C

3: pyridinium chlorochromate / dichloromethane / 22 h / 20 °C / Molecular sieve

4: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / tert-butyl alcohol / 4 h / 20 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 19 h / 20 °C

6: toluene-4-sulfonic acid / toluene / 24 h / 60 °C

7: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 5 h / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; 5%-palladium/activated carbon; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol;
DOI:10.1080/09168451.2020.1777081

Reference yield:

: (1R,2S,3S)-3-(4-benzyloxy-3-methoxybenzyl)-1-(4-benzyloxy-3-methoxyphenyl)-2-hydroxymethyl-1,4-butanediol

: 1002342-05-3
(3aS,4R,9aS)-3a,4,9,9a-tetrahydro-6-hydroxy-4-(4-hydroxy-3-methoxyphenyl)-7-methoxynaphtho[2,3-c]furan-1(3H)-one

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine / dichloromethane / 24 h / 20 °C

2: camphor-10-sulfonic acid / dichloromethane / 19 h / 20 °C

3: 2,6-dimethylpyridine / dichloromethane / 1 h / 20 °C

4: diisobutylaluminium hydride / toluene / 1 h / -10 °C

5: pyridinium chlorochromate / dichloromethane / 22 h / 20 °C / Molecular sieve

6: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / tert-butyl alcohol / 4 h / 20 °C

7: tetrabutyl ammonium fluoride / tetrahydrofuran / 19 h / 20 °C

8: toluene-4-sulfonic acid / toluene / 24 h / 60 °C

9: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; 5%-palladium/activated carbon; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; tert-butyl alcohol;
DOI:10.1080/09168451.2020.1777081