(E)-(2S,3R,4S,5S)-1-Benzyloxy-2,4-dimethyl-oct-6-ene-3,5-diol

Base Information

Chemical Name:(E)-(2S,3R,4S,5S)-1-Benzyloxy-2,4-dimethyl-oct-6-ene-3,5-diol
CAS No.:128146-35-0
Molecular Formula:C₁₇H₂₆O₃
Molecular Weight:278.392
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E)-(2S,3R,4S,5S)-1-Benzyloxy-2,4-dimethyl-oct-6-ene-3,5-diol

Chemical Property:

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Technology Process of (E)-(2S,3R,4S,5S)-1-Benzyloxy-2,4-dimethyl-oct-6-ene-3,5-diol

There total 13 articles about (E)-(2S,3R,4S,5S)-1-Benzyloxy-2,4-dimethyl-oct-6-ene-3,5-diol 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: 92.0%

: 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

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

Guidance literature:: With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -30 - -20 ℃; for 50.5h;
DOI:10.1021/ja00104a010

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With 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