(2E,4S,5S,6S,7S)-8-(benzyloxy)-4,6-(R)-(ethylidenedioxy)-5,7-dimethyl-2-octene

Base Information

Chemical Name:(2E,4S,5S,6S,7S)-8-(benzyloxy)-4,6-(R)-(ethylidenedioxy)-5,7-dimethyl-2-octene
CAS No.:160691-47-4
Molecular Formula:C₁₉H₂₈O₃
Molecular Weight:304.43
Hs Code.:

Synonyms:(2E,4S,5S,6S,7S)-8-(benzyloxy)-4,6-(R)-(ethylidenedioxy)-5,7-dimethyl-2-octene

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Chemical Property of (2E,4S,5S,6S,7S)-8-(benzyloxy)-4,6-(R)-(ethylidenedioxy)-5,7-dimethyl-2-octene

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Technology Process of (2E,4S,5S,6S,7S)-8-(benzyloxy)-4,6-(R)-(ethylidenedioxy)-5,7-dimethyl-2-octene

There total 6 articles about (2E,4S,5S,6S,7S)-8-(benzyloxy)-4,6-(R)-(ethylidenedioxy)-5,7-dimethyl-2-octene 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: 93.0%

: 534-15-6
1,1-dimethoxyethane

: 128146-35-0,128241-48-5
(2S,3S,4S,5S,6E)-1-(benzyloxy)-2,4-dimethyl-6-octene-3,5-diol

: 160691-47-4
(2E,4S,5S,6S,7S)-8-(benzyloxy)-4,6-(R)-(ethylidenedioxy)-5,7-dimethyl-2-octene

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; for 70h;
DOI:10.1021/ja00104a010

Reference yield:

: 116546-78-2
(S)-1-benzyloxy-2-methylpentan-3-one

: 160691-47-4
(2E,4S,5S,6S,7S)-8-(benzyloxy)-4,6-(R)-(ethylidenedioxy)-5,7-dimethyl-2-octene

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) (cyclohexyl)2BCl, Et₃N, 3.) 30percent aq. H₂O₂, pH 7 buffer

2: 92 percent / Me₄NHB(OAc)3, AcOH / acetonitrile / 50.5 h / -30 - -20 °C

3: 93 percent / p-TsOH / CH₂Cl₂ / 70 h

With pH 7 buffer; dicyclohexylboron chloride; dihydrogen peroxide; toluene-4-sulfonic acid; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetonitrile;
DOI:10.1021/ja00104a010

Reference yield:

: 116546-79-3,116661-38-2,128241-46-3,141611-63-4
(2S,4S,5S,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one

: 160691-47-4
(2E,4S,5S,6S,7S)-8-(benzyloxy)-4,6-(R)-(ethylidenedioxy)-5,7-dimethyl-2-octene

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / Me₄NHB(OAc)3, AcOH / acetonitrile / 50.5 h / -30 - -20 °C

2: 93 percent / p-TsOH / CH₂Cl₂ / 70 h

With toluene-4-sulfonic acid; acetic acid; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetonitrile;
DOI:10.1021/ja00104a010