(1S,3S,8aR)-6,6-(ethylenedioxy)-3-isopropenyl-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-1-tosyloxymethylnaphthalene

Base Information

Chemical Name:(1S,3S,8aR)-6,6-(ethylenedioxy)-3-isopropenyl-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-1-tosyloxymethylnaphthalene
CAS No.:160909-98-8
Molecular Formula:C₂₄H₃₂O₅S
Molecular Weight:432.581
Hs Code.:

Synonyms:

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Chemical Property of (1S,3S,8aR)-6,6-(ethylenedioxy)-3-isopropenyl-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-1-tosyloxymethylnaphthalene

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Technology Process of (1S,3S,8aR)-6,6-(ethylenedioxy)-3-isopropenyl-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-1-tosyloxymethylnaphthalene

There total 4 articles about (1S,3S,8aR)-6,6-(ethylenedioxy)-3-isopropenyl-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-1-tosyloxymethylnaphthalene 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: 96.0%

: 98-59-9
p-toluenesulfonyl chloride

: 160909-97-7
(1S,3S,8aR)-6,6-(ethylenedioxy)-3-isopropenyl-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenemethanol

: 160909-98-8
(1S,3S,8aR)-6,6-(ethylenedioxy)-3-isopropenyl-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-1-tosyloxymethylnaphthalene

Guidance literature:: With pyridine; for 2h;
DOI:10.1016/S0040-4020(01)89625-3

Reference yield:

: 160837-40-1
(1S,3S,4aS,8aR)-decahydro-4a-hydroxy-3-isopropenyl-8a-methyl-6-oxo-1-naphthalenecarbonitrile

: 160909-98-8
(1S,3S,8aR)-6,6-(ethylenedioxy)-3-isopropenyl-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-1-tosyloxymethylnaphthalene

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) p-toluenesulfonic acid / 1.) toluene, reflux, 1.5 h, 2.) toluene, reflux, 2 h

2: 95 percent / 1.2M diisobutylaluminum hydride / toluene / 1 h / -78 °C

3: 99 percent / sodium borohydride / ethanol / 0.5 h / 0 °C

4: 96 percent / pyridine / 2 h

With pyridine; sodium tetrahydroborate; diisobutylaluminium hydride; toluene-4-sulfonic acid; In ethanol; toluene;
DOI:10.1016/S0040-4020(01)89625-3

Reference yield:

: 160909-96-6
(1S,3S,8aR)-6,6-(ethylenedioxy)-3-isopropenyl-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenecarboxaldehyde

: 160909-98-8
(1S,3S,8aR)-6,6-(ethylenedioxy)-3-isopropenyl-8a-methyl-1,2,3,5,6,7,8,8a-octahydro-1-tosyloxymethylnaphthalene

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / sodium borohydride / ethanol / 0.5 h / 0 °C

2: 96 percent / pyridine / 2 h

With pyridine; sodium tetrahydroborate; In ethanol;
DOI:10.1016/S0040-4020(01)89625-3