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

Base Information

• Chemical Name: (2S,4S,5R,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one
• CAS No.: 141611-63-4
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 141611-63-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (2S,4S,5R,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one 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%

trans-Crotonaldehyde (123-73-9,4170-30-3) + (S)-1-benzyloxy-2-methylpentan-3-one (116546-78-2) → (2S,4R,5S,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one (160796-66-7) + (2S,4S,5R,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one (141611-63-4)

Guidance literature:

(S)-1-benzyloxy-2-methylpentan-3-one; With titanium(IV) isopropylate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.5h;

trans-Crotonaldehyde; In dichloromethane; at -78 ℃;

DOI:10.1021/jo050792l

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (2S,4S,5R,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one (141611-63-4)

Guidance literature:

Multi-step reaction with 4 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

With trifluorormethanesulfonic acid; pH 7 buffer; dihydrogen peroxide; trimethylaluminum; (+)-diisopinocampheylborane trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1021/ja00104a010

Reference yield:

Weinreb amide of (S)-3-benzyloxy-2-methylpropionic acid (116652-76-7) → (2S,4S,5R,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one (141611-63-4)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 1 h / 0 °C

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

With pH 7 buffer; dihydrogen peroxide; (+)-diisopinocampheylborane trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;

DOI:10.1021/ja00104a010

upstream raw materials:

trans-Crotonaldehyde

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

(+)-diisopinocampheylborane trifluoromethanesulfonate

O-benzyl 2,2,2-trichloroacetimidate

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