(S)-Acetoxy-phenyl-acetic acid (2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

Base Information

Chemical Name:(S)-Acetoxy-phenyl-acetic acid (2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester
CAS No.:897041-87-1
Molecular Formula:C₂₉H₃₂O₇
Molecular Weight:492.569
Hs Code.:

Synonyms:(S)-Acetoxy-phenyl-acetic acid (2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

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Chemical Property of (S)-Acetoxy-phenyl-acetic acid (2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

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Technology Process of (S)-Acetoxy-phenyl-acetic acid (2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

There total 9 articles about (S)-Acetoxy-phenyl-acetic acid (2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl 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:

: [(2R,6S,8aS)-2-(4-Methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-yl]-methanol

: 7322-88-5
(S)-acetylmandelic acid

: 897041-87-1
(S)-Acetoxy-phenyl-acetic acid (2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

: (S)-Acetoxy-phenyl-acetic acid (2S,6R,8aR)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 1.5h;
DOI:10.1021/ja060847g

Reference yield:

: (1R,5R)-5-Methyl-3-oxo-2-oxa-bicyclo[3.2.2]non-6-ene-6,7-dicarboxylic acid dimethyl ester

: 897041-87-1
(S)-Acetoxy-phenyl-acetic acid (2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 100 percent / camphorsulfonic acid / 16 h / Heating

2.1: 84 percent / camphorsulfonic acid / CH₂Cl₂ / 36 h

3.1: 65 percent / lithium aluminum hydride / diethyl ether / 5 h / 0 - 20 °C

4.1: 80 percent / pyridinium p-toluenesulfonic acid / CH₂Cl₂ / 19 h

5.1: o-nitrophenylselenocyanate; tri-n-butylphosphine / tetrahydrofuran / 1 h / 0 °C

5.2: 71 percent / aq. H₂O₂ / tetrahydrofuran / 3 h / 0 - 45 °C

6.1: 82 percent / pyridinium p-toluenesulfonic acid / methanol / 2 h

7.1: 69 percent / DDQ / CH₂Cl₂ / 0.5 h / 20 °C

8.1: N,N-dimethylaminopyridine; dicyclohexylacarbodiimide / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; tributylphosphine; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja060847g

Reference yield:

: (1R,4R)-1-Methyl-5-oxo-bicyclo[2.2.2]oct-2-ene-2,3-dicarboxylic acid dimethyl ester

: 897041-87-1
(S)-Acetoxy-phenyl-acetic acid (2R,6S,8aS)-2-(4-methoxy-phenyl)-6-methyl-6-vinyl-6,7,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 96 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 12 h / 20 °C

2.1: 100 percent / camphorsulfonic acid / 16 h / Heating

3.1: 84 percent / camphorsulfonic acid / CH₂Cl₂ / 36 h

4.1: 65 percent / lithium aluminum hydride / diethyl ether / 5 h / 0 - 20 °C

5.1: 80 percent / pyridinium p-toluenesulfonic acid / CH₂Cl₂ / 19 h

6.1: o-nitrophenylselenocyanate; tri-n-butylphosphine / tetrahydrofuran / 1 h / 0 °C

6.2: 71 percent / aq. H₂O₂ / tetrahydrofuran / 3 h / 0 - 45 °C

7.1: 82 percent / pyridinium p-toluenesulfonic acid / methanol / 2 h

8.1: 69 percent / DDQ / CH₂Cl₂ / 0.5 h / 20 °C

9.1: N,N-dimethylaminopyridine; dicyclohexylacarbodiimide / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; tributylphosphine; camphor-10-sulfonic acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja060847g