(3R,5S)-6-benzyloxy-3,5-dimethylhexan-2-ol

Base Information

• Chemical Name: (3R,5S)-6-benzyloxy-3,5-dimethylhexan-2-ol
• CAS No.: 1253642-71-5
• Molecular Formula: C₁₅H₂₄O₂
• Molecular Weight: 236.354
• Mol file: 1253642-71-5.mol

Synonyms:

Chemical Property of (3R,5S)-6-benzyloxy-3,5-dimethylhexan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-6-benzyloxy-3,5-dimethylhexan-2-ol

There total 7 articles about (3R,5S)-6-benzyloxy-3,5-dimethylhexan-2-ol 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: 80.0%

(2R,4S)-5-benzyloxy-2,4-dimethylpentanal + methylmagnesium bromide (75-16-1) → (3R,5S)-6-benzyloxy-3,5-dimethylhexan-2-ol (1253642-71-5)

Guidance literature:

In diethyl ether; at -78 - 23 ℃;

DOI:10.1021/ja1073432

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (3R,5S)-6-benzyloxy-3,5-dimethylhexan-2-ol (1253642-71-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C

1.2: 6 h / 0 °C

2.1: lithium borohydride / tetrahydrofuran; methanol / 2 h / 0 - 25 °C

3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2 h / 23 °C

4.1: n-butyllithium; diisopropylamine; lithium chloride / tetrahydrofuran; hexane / 1.33 h / -78 - 23 °C

4.2: 0 °C

5.1: n-butyllithium; borane-ammonia complex; diisopropylamine / tetrahydrofuran; hexane / 2 h / 0 - 23 °C

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

6.2: 1 h / -78 °C

7.1: diethyl ether / -78 - 23 °C

With 1H-imidazole; lithium borohydride; n-butyllithium; borane-ammonia complex; oxalyl dichloride; iodine; titanium tetrachloride; dimethyl sulfoxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 6.1: Swern oxidation / 6.2: Swern oxidation;

DOI:10.1021/ja1073432

Reference yield:

(S)-3-benzyloxy-2-methylpropan-1-ol (63930-46-1) → (3R,5S)-6-benzyloxy-3,5-dimethylhexan-2-ol (1253642-71-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2 h / 23 °C

2.1: n-butyllithium; diisopropylamine; lithium chloride / tetrahydrofuran; hexane / 1.33 h / -78 - 23 °C

2.2: 0 °C

3.1: n-butyllithium; borane-ammonia complex; diisopropylamine / tetrahydrofuran; hexane / 2 h / 0 - 23 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

4.2: 1 h / -78 °C

5.1: diethyl ether / -78 - 23 °C

With 1H-imidazole; n-butyllithium; borane-ammonia complex; oxalyl dichloride; iodine; dimethyl sulfoxide; diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 4.1: Swern oxidation / 4.2: Swern oxidation;

DOI:10.1021/ja1073432

upstream raw materials:

methylmagnesium bromide

Benzyloxymethyl chloride

(S)-3-benzyloxy-2-methylpropan-1-ol

(4S,2'R)-3-(3'-(benzyloxy)-2'-methylpropanoyl)-4-benzyl-1,3-oxazolidin-2-one