1-[(2S,3aS,4R,6aS,9aS,9bR)-4-Hydroxy-2-(4-methoxy-phenyl)-4,7,7,9b-tetramethyl-octahydro-naphtho[1,8-de][1,3]dioxin-3a-yl]-but-2-yn-1-one

Base Information

Chemical Name:1-[(2S,3aS,4R,6aS,9aS,9bR)-4-Hydroxy-2-(4-methoxy-phenyl)-4,7,7,9b-tetramethyl-octahydro-naphtho[1,8-de][1,3]dioxin-3a-yl]-but-2-yn-1-one
CAS No.:136321-12-5
Molecular Formula:C₂₆H₃₄O₅
Molecular Weight:426.553
Hs Code.:

Synonyms:1-[(2S,3aS,4R,6aS,9aS,9bR)-4-Hydroxy-2-(4-methoxy-phenyl)-4,7,7,9b-tetramethyl-octahydro-naphtho[1,8-de][1,3]dioxin-3a-yl]-but-2-yn-1-one

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Chemical Property of 1-[(2S,3aS,4R,6aS,9aS,9bR)-4-Hydroxy-2-(4-methoxy-phenyl)-4,7,7,9b-tetramethyl-octahydro-naphtho[1,8-de][1,3]dioxin-3a-yl]-but-2-yn-1-one

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Technology Process of 1-[(2S,3aS,4R,6aS,9aS,9bR)-4-Hydroxy-2-(4-methoxy-phenyl)-4,7,7,9b-tetramethyl-octahydro-naphtho[1,8-de][1,3]dioxin-3a-yl]-but-2-yn-1-one

There total 8 articles about 1-[(2S,3aS,4R,6aS,9aS,9bR)-4-Hydroxy-2-(4-methoxy-phenyl)-4,7,7,9b-tetramethyl-octahydro-naphtho[1,8-de][1,3]dioxin-3a-yl]-but-2-yn-1-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: 68.0%

: 136320-97-3,136377-88-3
(2S,3aR,4R,6aS,9aS,9bR)-3a-(1-Hydroxy-but-2-ynyl)-2-(4-methoxy-phenyl)-4,7,7,9b-tetramethyl-decahydro-naphtho[1,8-de][1,3]dioxin-4-ol

: 136321-12-5
1-[(2S,3aS,4R,6aS,9aS,9bR)-4-Hydroxy-2-(4-methoxy-phenyl)-4,7,7,9b-tetramethyl-octahydro-naphtho[1,8-de][1,3]dioxin-3a-yl]-but-2-yn-1-one

Guidance literature:: With pyridine-SO₃ complex; triethylamine; In dimethyl sulfoxide; for 3h;
DOI:10.1016/0040-4039(91)80618-G

Reference yield:

: 98-88-4
benzoyl chloride

: 136321-12-5
1-[(2S,3aS,4R,6aS,9aS,9bR)-4-Hydroxy-2-(4-methoxy-phenyl)-4,7,7,9b-tetramethyl-octahydro-naphtho[1,8-de][1,3]dioxin-3a-yl]-but-2-yn-1-one

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / DMAP, pyridine / 2 h

2: TsOH / 0.17 h

3: HC(OMe)3, TsOH

4: 94 percent / K₂CO₃ / methanol / 3 h / 60 °C

5: 87 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide / 3 h

7: 1) DDQ, 2) K₂CO₃ / 1) CH₂Cl₂, 0 deC, 10 h, 2) MeOH, 2.5 h

8: 68 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide / 3 h

With pyridine; dmap; pyridine-SO₃ complex; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; trimethyl orthoformate; In methanol; dimethyl sulfoxide;
DOI:10.1016/0040-4039(91)80618-G

Reference yield:

: 136320-89-3
(2S,3aS,5aR,9R,9aS,9bR)-2-Methoxy-9-(4-methoxy-benzyloxy)-3a,6,6,9a-tetramethyl-octahydro-naphtho[1,2-d][1,3]dioxole-9b-carbaldehyde

: 136321-12-5
1-[(2S,3aS,4R,6aS,9aS,9bR)-4-Hydroxy-2-(4-methoxy-phenyl)-4,7,7,9b-tetramethyl-octahydro-naphtho[1,8-de][1,3]dioxin-3a-yl]-but-2-yn-1-one

Guidance literature:: Multi-step reaction with 3 steps

2: 1) DDQ, 2) K₂CO₃ / 1) CH₂Cl₂, 0 deC, 10 h, 2) MeOH, 2.5 h

3: 68 percent / SO₃*pyridine, Et₃N / dimethylsulfoxide / 3 h

With pyridine-SO₃ complex; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dimethyl sulfoxide;
DOI:10.1016/0040-4039(91)80618-G