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

Base Information

• Chemical Name: 2-((R)-6-Hydroxy-tetrahydro-pyran-2-yl)-2-methyl-propionic acid benzyl ester
• CAS No.: 404890-54-6
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 404890-54-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about 2-((R)-6-Hydroxy-tetrahydro-pyran-2-yl)-2-methyl-propionic 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: 96.0%

2-Methyl-2-((R)-6-oxo-tetrahydro-pyran-2-yl)-propionic acid benzyl ester (404890-52-4) → 2-((R)-6-Hydroxy-tetrahydro-pyran-2-yl)-2-methyl-propionic acid benzyl ester (404890-54-6)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/ol016938u

Reference yield: 79.0%

2-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-propionic acid benzyl ester (404890-51-3) → 2-((R)-6-Hydroxy-tetrahydro-pyran-2-yl)-2-methyl-propionic acid benzyl ester (404890-54-6) + 2-Methyl-2-((R)-6-oxo-tetrahydro-pyran-2-yl)-propionic acid benzyl ester (404890-52-4)

Guidance literature:

With sodium tetrahydroborate; nickel dichloride; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/ol016938u

Reference yield:

benzyl 2,2-dimethyl-3-oxopropanoate (97518-80-4) → 2-((R)-6-Hydroxy-tetrahydro-pyran-2-yl)-2-methyl-propionic acid benzyl ester (404890-54-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: (+)-Ipc₂BOMe / diethyl ether / 3 h / -78 - 20 °C

1.2: 79 percent / diethyl ether / 4 h / -78 °C

2.1: 83 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 1 h / 0 °C

3.1: 76 percent / Grubbs' imidazolidinyl ruthenium complex / CH₂Cl₂ / 4 h / 20 °C

4.1: 7 percent / NaBH₄ / NiCl₂*6H₂O / tetrahydrofuran / 2 h / 0 °C

With dmap; sodium tetrahydroborate; N-ethyl-N,N-diisopropylamine; (+)-B-methoxydiisocamphenylborane; Grubbs catalyst first generation; nickel dichloride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ol016938u

upstream raw materials:

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

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

benzyl 2,2-dimethyl-3-oxopropanoate

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

Downstream raw materials:

(E)-(R)-3-Hydroxy-2,2-dimethyl-9-oxo-dec-7-enoic acid benzyl ester

2-Methyl-2-[(2R,6S)-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-propionic acid benzyl ester

2-Methyl-2-[(2R,6R)-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-propionic acid benzyl ester

2-{(2R,6S)-6-[(4R,5S)-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