(R)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester

Base Information

• Chemical Name: (R)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester
• CAS No.: 404890-49-9
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 404890-49-9.mol

Synonyms:(R)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester

Chemical Property of (R)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester

There total 1 articles about (R)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester 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: 79.0%

benzyl 2,2-dimethyl-3-oxopropanoate (97518-80-4) + allylmagnesium bromide (1730-25-2) → (R)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester (404890-49-9) + (S)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester

Guidance literature:

allylmagnesium bromide; With (+)-B-methoxydiisocamphenylborane; In diethyl ether; at -78 - 20 ℃; for 3h;

benzyl 2,2-dimethyl-3-oxopropanoate; In diethyl ether; at -78 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1021/ol016938u

Reference yield: 83.0%

acryloyl chloride (814-68-6,25189-84-8) + (R)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester (404890-49-9) → (R)-3-Acryloyloxy-2,2-dimethyl-hex-5-enoic acid benzyl ester (404890-50-2)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ol016938u

Reference yield:

(R)-3-Hydroxy-2,2-dimethyl-hex-5-enoic acid benzyl ester (404890-49-9) → 2-{(2R,6S)-6-[(4S,5R)-7-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-4-hydroxy-5-methyl-2-oxo-heptyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester

Guidance literature:

Multi-step reaction with 6 steps

1.1: 83 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 1 h / 0 °C

2.1: 76 percent / Grubbs' imidazolidinyl ruthenium complex / CH₂Cl₂ / 4 h / 20 °C

3.1: 7 percent / NaBH₄ / NiCl₂*6H₂O / tetrahydrofuran / 2 h / 0 °C

4.1: 70 percent / acetonitrile / 24 h / 90 °C

5.1: 90 percent / t-BuOK / tetrahydrofuran / 0.17 h / 0 °C

6.1: Et₂BOTf; i-Pr₂NEt / diethyl ether; hexane / -78 °C

6.2: diethyl ether; hexane / -78 °C

With dmap; sodium tetrahydroborate; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; Grubbs catalyst first generation; nickel dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;

DOI:10.1021/ol016938u

upstream raw materials:

benzyl 2,2-dimethyl-3-oxopropanoate

allylmagnesium bromide

Downstream raw materials:

(R)-3-Acryloyloxy-2,2-dimethyl-hex-5-enoic acid benzyl ester

2-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-propionic acid benzyl ester

2-((R)-6-Hydroxy-tetrahydro-pyran-2-yl)-2-methyl-propionic acid benzyl ester

2-Methyl-2-((R)-6-oxo-tetrahydro-pyran-2-yl)-propionic acid benzyl ester