(3aR,4R,5S,6S,7S,7aS)-5-ethenylhexahydro-2,2,4-trimethyl-9-methylene-6-(phenylmethoxy)-4,7-ethano-1,3-benzodioxol-5-ol

Base Information

Chemical Name:(3aR,4R,5S,6S,7S,7aS)-5-ethenylhexahydro-2,2,4-trimethyl-9-methylene-6-(phenylmethoxy)-4,7-ethano-1,3-benzodioxol-5-ol
CAS No.:210633-94-6
Molecular Formula:C₂₂H₂₈O₄
Molecular Weight:356.462
Hs Code.:

Synonyms:(3aR,4R,5S,6S,7S,7aS)-5-ethenylhexahydro-2,2,4-trimethyl-9-methylene-6-(phenylmethoxy)-4,7-ethano-1,3-benzodioxol-5-ol

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Chemical Property of (3aR,4R,5S,6S,7S,7aS)-5-ethenylhexahydro-2,2,4-trimethyl-9-methylene-6-(phenylmethoxy)-4,7-ethano-1,3-benzodioxol-5-ol

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Technology Process of (3aR,4R,5S,6S,7S,7aS)-5-ethenylhexahydro-2,2,4-trimethyl-9-methylene-6-(phenylmethoxy)-4,7-ethano-1,3-benzodioxol-5-ol

There total 7 articles about (3aR,4R,5S,6S,7S,7aS)-5-ethenylhexahydro-2,2,4-trimethyl-9-methylene-6-(phenylmethoxy)-4,7-ethano-1,3-benzodioxol-5-ol 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: 53.0%

: 100-39-0
benzyl bromide

: 210633-93-5
(3aR,4R,5S,6S,7S,7aS)-5-ethenylhexahydro-2,2,4-trimethyl-9-methylene-4,7-ethano-1,3-benzodioxole-5,6-diol

: 210633-94-6
(3aR,4R,5S,6S,7S,7aS)-5-ethenylhexahydro-2,2,4-trimethyl-9-methylene-6-(phenylmethoxy)-4,7-ethano-1,3-benzodioxol-5-ol

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 5h;
DOI:10.1071/CH03164

Reference yield:

: 685108-94-5
(3aS,4R,4aS,6S,7aR,8S,8aR)-hexahydro-6-(4-methoxyphenyl)-2,2,8-trimethyl-4,8-ethanobenzo[1,2-d:4,5-d']bis[1,3]-dioxol-9-one

: 210633-94-6
(3aR,4R,5S,6S,7S,7aS)-5-ethenylhexahydro-2,2,4-trimethyl-9-methylene-6-(phenylmethoxy)-4,7-ethano-1,3-benzodioxol-5-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / dimethylsulfoxide / 16 h / 65 °C

2.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 5 h / 18 °C

2.2: 1.40 g / trifluoroacetic anhydride; dimethylsulfoxide / CH₂Cl₂ / 4 h / -60 °C

3.1: tetrahydrofuran / 0 - 18 °C

3.2: 11 percent / potassium hydroxide / methanol / 16 h / 18 °C

4.1: 53 percent / sodium hydride / dimethylformamide / 5 h / 0 °C

With sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; 1.1: Wittig reaction / 2.2: Swern oxidation;
DOI:10.1071/CH03164

Reference yield:

: 685108-95-6
(3aR,4S,4aR,6S,7aS,8R,8aS)-hexahydro-6-(4-methoxyphenyl)-2,2,4-trimethyl-10-methylene-4,8-ethanobenzo[1,2-d:4,5-d']bis[1,3]dioxole

: 210633-94-6
(3aR,4R,5S,6S,7S,7aS)-5-ethenylhexahydro-2,2,4-trimethyl-9-methylene-6-(phenylmethoxy)-4,7-ethano-1,3-benzodioxol-5-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 5 h / 18 °C

1.2: 1.40 g / trifluoroacetic anhydride; dimethylsulfoxide / CH₂Cl₂ / 4 h / -60 °C

2.1: tetrahydrofuran / 0 - 18 °C

2.2: 11 percent / potassium hydroxide / methanol / 16 h / 18 °C

3.1: 53 percent / sodium hydride / dimethylformamide / 5 h / 0 °C

With sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.2: Swern oxidation;
DOI:10.1071/CH03164