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

Base Information

• Chemical Name: 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
• CAS No.: 858346-72-2
• Molecular Formula: C₃₄H₅₂O₇
• Molecular Weight: 572.783
• Mol file: 858346-72-2.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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: 82.0%

acetaldehyde (75-07-0,9002-91-9) + 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) → 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 (858346-72-2)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 0 ℃; for 8h;

DOI:10.1021/ol0510769

Reference yield: 95.0%

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 (858346-72-2) + chloromethyl methyl ether (107-30-2) → 2-{(2R,6S)-6-[(2S,4R,5S)-4-Acetoxy-7-((2S,6R)-6-allyl-tetrahydro-pyran-2-yl)-2-methoxymethoxy-5-methyl-heptyl]-tetrahydro-pyran-2-yl}-2-methyl-propionic acid benzyl ester (858346-73-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 - 50 ℃; for 15h;

DOI:10.1021/ol0510769

Reference yield:

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 (858346-72-2) → 2-[(2R,6S)-6-((2S,4R,5S)-2-Methoxymethoxy-5-methyl-7-{(2S,6S)-6-[3-(4-oxo-2,2-diphenyl-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-trimethylsilanyloxy-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / iPr₂NEt / CH₂Cl₂ / 15 h / 20 - 50 °C

2: 70 percent / K₂CO₃; methanol / 60 h / 20 °C

3: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

4: tetrahydrofuran / 12 h / 20 °C

5: K₃PO₄ / PdCl₂(dppf) / tetrahydrofuran; dimethylformamide; H₂O / 20 h / 20 °C

With methanol; potassium phosphate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 5: Suzuki-Miyaura reaction;

DOI:10.1021/ol0510769

upstream raw materials:

acetaldehyde

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

Downstream raw materials:

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

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

2-[(2R,6S)-6-((2R,4R,5S)-7-{(2S,6S)-6-[3-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-2-methoxymethoxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester