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

Base Information

• Chemical Name: 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
• CAS No.: 404890-72-8
• Molecular Formula: C₃₂H₄₈O₆
• Molecular Weight: 528.73
• Mol file: 404890-72-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 15 articles about 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 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:

benzyl 2,2-dimethyl-3-oxopropanoate (97518-80-4) → 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 (404890-72-8)

Guidance literature:

Multi-step reaction with 7 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

5.1: 70 percent / acetonitrile / 24 h / 90 °C

6.1: 90 percent / t-BuOK / tetrahydrofuran / 0.17 h / 0 °C

7.1: Chx₂BCl; Et₃N / diethyl ether / -78 °C

7.2: diethyl ether / -78 °C

With dmap; sodium tetrahydroborate; dicyclohexylboron chloride; potassium tert-butylate; triethylamine; N-ethyl-N,N-diisopropylamine; (+)-B-methoxydiisocamphenylborane; Grubbs catalyst first generation; nickel dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

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-[(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 (404890-72-8)

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: Chx₂BCl; Et₃N / diethyl ether / -78 °C

6.2: diethyl ether / -78 °C

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

DOI:10.1021/ol016938u

Reference yield:

2-methyl-2-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-propionic acid benzyl ester (404890-51-3) → 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 (404890-72-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 7 percent / NaBH₄ / NiCl₂*6H₂O / tetrahydrofuran / 2 h / 0 °C

2.1: 70 percent / acetonitrile / 24 h / 90 °C

3.1: 90 percent / t-BuOK / tetrahydrofuran / 0.17 h / 0 °C

4.1: Chx₂BCl; Et₃N / diethyl ether / -78 °C

4.2: diethyl ether / -78 °C

With sodium tetrahydroborate; dicyclohexylboron chloride; potassium tert-butylate; triethylamine; nickel dichloride; In tetrahydrofuran; diethyl ether; acetonitrile;

DOI:10.1021/ol016938u

upstream raw materials:

(S)-4-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-2-methyl-butyraldehyde

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

benzyl 2,2-dimethyl-3-oxopropanoate

((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-acetaldehyde

Downstream raw materials:

2-{(2R,6S)-6-[(2S,4R,5S)-4-Acetoxy-7-((2S,6R)-6-allyl-tetrahydro-pyran-2-yl)-2-hydroxy-5-methyl-heptyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester

2-{(2R,6S)-6-[(2R,4R,5S)-7-((2S,6R)-6-Allyl-tetrahydro-pyran-2-yl)-2,4-dihydroxy-5-methyl-heptyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester

benzophenone

2-[6-(2-(tert-butyl-dimethyl-silanyloxy)-5-methyl-7-{6-[3-(4-oxo-2,2-diphenyl-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-trifluoroacetoxy-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester