(1R,4aS,5S,6S,8aS)-6-Benzyloxy-3,3-dimethoxy-5,8a-dimethyl-decahydro-naphthalene-1-carbonitrile

Base Information

Chemical Name:(1R,4aS,5S,6S,8aS)-6-Benzyloxy-3,3-dimethoxy-5,8a-dimethyl-decahydro-naphthalene-1-carbonitrile
CAS No.:104996-12-5
Molecular Formula:C₂₂H₃₁NO₃
Molecular Weight:357.493
Hs Code.:

Synonyms:(1R,4aS,5S,6S,8aS)-6-Benzyloxy-3,3-dimethoxy-5,8a-dimethyl-decahydro-naphthalene-1-carbonitrile

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Chemical Property of (1R,4aS,5S,6S,8aS)-6-Benzyloxy-3,3-dimethoxy-5,8a-dimethyl-decahydro-naphthalene-1-carbonitrile

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Technology Process of (1R,4aS,5S,6S,8aS)-6-Benzyloxy-3,3-dimethoxy-5,8a-dimethyl-decahydro-naphthalene-1-carbonitrile

There total 6 articles about (1R,4aS,5S,6S,8aS)-6-Benzyloxy-3,3-dimethoxy-5,8a-dimethyl-decahydro-naphthalene-1-carbonitrile 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: 83.0%

: 78-39-7
Triethyl orthoacetate

: 104996-11-4
(1R,4aS,5S,6S,8aS)-6-Benzyloxy-5,8a-dimethyl-3-oxo-decahydro-naphthalene-1-carbonitrile

: 104996-12-5
(1R,4aS,5S,6S,8aS)-6-Benzyloxy-3,3-dimethoxy-5,8a-dimethyl-decahydro-naphthalene-1-carbonitrile

Guidance literature:: With toluene-4-sulfonic acid; In methanol; for 24h; Ambient temperature;
DOI:10.1021/jo00374a016

Reference yield:

: 104996-08-9,104996-09-0
(4aS,7R,8R,8aR)-7-Benzyloxy-4a,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-ol

: 104996-12-5
(1R,4aS,5S,6S,8aS)-6-Benzyloxy-3,3-dimethoxy-5,8a-dimethyl-decahydro-naphthalene-1-carbonitrile

Guidance literature:: Multi-step reaction with 3 steps

1: MnO₂ / CH₂Cl₂ / 18 h / Ambient temperature

2: 74 percent / NH₄Cl / dimethylformamide; H₂O / 3 h / 70 - 80 °C

3: 83 percent / p-TsOH / methanol / 24 h / Ambient temperature

With manganese(IV) oxide; ammonium chloride; toluene-4-sulfonic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00374a016

Reference yield:

: 104996-06-7
(4aS,5S,6S,8aS)-6-Benzyloxy-5,8a-dimethyl-4a,5,6,7,8,8a-hexahydro-4H-naphthalen-1-one

: 104996-12-5
(1R,4aS,5S,6S,8aS)-6-Benzyloxy-3,3-dimethoxy-5,8a-dimethyl-decahydro-naphthalene-1-carbonitrile

Guidance literature:: Multi-step reaction with 5 steps

1: 30percent hydrogen peroxide, 6 N aq. sodium hydroxide / methanol / 3 h / Ambient temperature

2: 95percent hydrazine, glacial acetic acid / methanol / 2 h / Heating

3: MnO₂ / CH₂Cl₂ / 18 h / Ambient temperature

4: 74 percent / NH₄Cl / dimethylformamide; H₂O / 3 h / 70 - 80 °C

5: 83 percent / p-TsOH / methanol / 24 h / Ambient temperature

With manganese(IV) oxide; sodium hydroxide; dihydrogen peroxide; ammonium chloride; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00374a016