(4S,4aS,7S,8S,8aS)-7-Benzyloxy-4-hydroxymethyl-4a,8-dimethyl-octahydro-naphthalen-2-one

Base Information

Chemical Name:(4S,4aS,7S,8S,8aS)-7-Benzyloxy-4-hydroxymethyl-4a,8-dimethyl-octahydro-naphthalen-2-one
CAS No.:104996-16-9
Molecular Formula:C₂₀H₂₈O₃
Molecular Weight:316.441
Hs Code.:

Synonyms:(4S,4aS,7S,8S,8aS)-7-Benzyloxy-4-hydroxymethyl-4a,8-dimethyl-octahydro-naphthalen-2-one

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Chemical Property of (4S,4aS,7S,8S,8aS)-7-Benzyloxy-4-hydroxymethyl-4a,8-dimethyl-octahydro-naphthalen-2-one

Chemical Property:

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Technology Process of (4S,4aS,7S,8S,8aS)-7-Benzyloxy-4-hydroxymethyl-4a,8-dimethyl-octahydro-naphthalen-2-one

There total 10 articles about (4S,4aS,7S,8S,8aS)-7-Benzyloxy-4-hydroxymethyl-4a,8-dimethyl-octahydro-naphthalen-2-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:

: 104996-15-8
((1S,4aS,5S,6S,8aS)-6-Benzyloxy-3,3-dimethoxy-5,8a-dimethyl-decahydro-naphthalen-1-yl)-methanol

: 104996-16-9
(4S,4aS,7S,8S,8aS)-7-Benzyloxy-4-hydroxymethyl-4a,8-dimethyl-octahydro-naphthalen-2-one

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 25 ℃; for 3.5h; Yield given;
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

: 104996-16-9
(4S,4aS,7S,8S,8aS)-7-Benzyloxy-4-hydroxymethyl-4a,8-dimethyl-octahydro-naphthalen-2-one

Guidance literature:: Multi-step reaction with 7 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

4: KOH / bis-(2-hydroxy-ethyl) ether / 36 h / 200 °C

5: diethyl ether

6: LiAlH₄ / diethyl ether / 2.5 h

7: p-toluenesulfonic acid / acetone / 3.5 h / 25 °C

With manganese(IV) oxide; potassium hydroxide; lithium aluminium tetrahydride; ammonium chloride; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; diethylene glycol;
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

: 104996-16-9
(4S,4aS,7S,8S,8aS)-7-Benzyloxy-4-hydroxymethyl-4a,8-dimethyl-octahydro-naphthalen-2-one

Guidance literature:: Multi-step reaction with 9 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

6: KOH / bis-(2-hydroxy-ethyl) ether / 36 h / 200 °C

7: diethyl ether

8: LiAlH₄ / diethyl ether / 2.5 h

9: p-toluenesulfonic acid / acetone / 3.5 h / 25 °C

With manganese(IV) oxide; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; dihydrogen peroxide; ammonium chloride; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; diethylene glycol;
DOI:10.1021/jo00374a016