(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
• Mol file: 128146-35-0.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

(2S,4S,5S,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one (116546-79-3,116661-38-2,128241-46-3,141611-63-4) → (2S,3S,4S,5S,6E)-1-(benzyloxy)-2,4-dimethyl-6-octene-3,5-diol (128146-35-0,128241-48-5)

Guidance literature:

With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -30 - -20 ℃; for 50.5h;

DOI:10.1021/ja00104a010

Reference yield:

(S)-1-benzyloxy-2-methylpentan-3-one (116546-78-2) → (2S,3S,4S,5S,6E)-1-(benzyloxy)-2,4-dimethyl-6-octene-3,5-diol (128146-35-0,128241-48-5)

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:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (2S,3S,4S,5R,6E)-1-(benzyloxy)-2,4-dimethyl-6-octene-3,5-diol (128146-35-0,128241-48-5)

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

upstream raw materials:

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

O-benzyl 2,2,2-trichloroacetimidate

methyl (S)-3-benzyloxy-2-methylpropanoate

(S)-1-benzyloxy-2-methylpentan-3-one

Downstream raw materials:

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

(2S,3R,4S,5S,6R)-6-<(benzyloxy)methoxy>-2,4-bis(tert-butyldimethylsiloxy)-3,5-dimethylheptanal

(2E,4R,5S,6S,7S,8R)-8-<(benzyloxy)methoxy>-4,6-bis(tert-butyldimethylsiloxy)-5,7-dimethyl-7-nonene

C₄₁H₆₉Cl₃O₉Si₂