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

Base Information

Chemical Name:(2E,4R,5S,6S,7S)-8-(benzyloxy)-4,6-bis(tert-butyldimethylsiloxy)-5,7-dimethyl-2-octene
CAS No.:160691-31-6
Molecular Formula:C₂₉H₅₄O₃Si₂
Molecular Weight:506.917
Hs Code.:

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

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

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

There total 6 articles about (2E,4R,5S,6S,7S)-8-(benzyloxy)-4,6-bis(tert-butyldimethylsiloxy)-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: 86.0%

: 69739-34-0
t-butyldimethylsiyl triflate

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

: 160691-31-6
(2E,4R,5S,6S,7S)-8-(benzyloxy)-4,6-bis(tert-butyldimethylsiloxy)-5,7-dimethyl-2-octene

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.75h;
DOI:10.1021/ja00104a010

Reference yield:

: 141611-63-4
(2S,4S,5R,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one

: 160691-31-6
(2E,4R,5S,6S,7S)-8-(benzyloxy)-4,6-bis(tert-butyldimethylsiloxy)-5,7-dimethyl-2-octene

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) n-Bu₂BOMe, 2.) LiBH₄, 3.) pH 7 buffer, aq. H₂O₂

2: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 °C

With 2,6-dimethylpyridine; lithium borohydride; pH 7 buffer; dibutylborinic acid methyl ester; dihydrogen peroxide; In dichloromethane;
DOI:10.1021/ja00104a010

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 160691-31-6
(2E,4R,5S,6S,7S)-8-(benzyloxy)-4,6-bis(tert-butyldimethylsiloxy)-5,7-dimethyl-2-octene

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / TfOH / CH₂Cl₂; cyclohexane / 16 h / Ambient temperature

2: 1.) Me₃Al / 1.) toluene, from 0 deg C to RT, 15 min, 2.) toluene, from 70 to 80 deg C, 2 h

3: tetrahydrofuran / 1 h / 0 °C

4: 1.) (-)-(Ipc)2BOTf, diisopropylethylamine, 3.) 30percent aq. H₂O₂, pH 7 buffer

5: 1.) n-Bu₂BOMe, 2.) LiBH₄, 3.) pH 7 buffer, aq. H₂O₂

6: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 °C

With 2,6-dimethylpyridine; lithium borohydride; trifluorormethanesulfonic acid; pH 7 buffer; dibutylborinic acid methyl ester; dihydrogen peroxide; trimethylaluminum; (+)-diisopinocampheylborane trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; cyclohexane;
DOI:10.1021/ja00104a010