(S)-1-((S)-1-(benzyloxy)-14-methyl-1-oxopentadecan-3-yl) 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate

Base Information

• Chemical Name: (S)-1-((S)-1-(benzyloxy)-14-methyl-1-oxopentadecan-3-yl) 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate
• CAS No.: 1402050-37-6
• Molecular Formula: C₃₈H₆₂O₁₀
• Molecular Weight: 678.904
• Mol file: 1402050-37-6.mol

Synonyms:(S)-1-((S)-1-(benzyloxy)-14-methyl-1-oxopentadecan-3-yl) 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate

Chemical Property of (S)-1-((S)-1-(benzyloxy)-14-methyl-1-oxopentadecan-3-yl) 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((S)-1-(benzyloxy)-14-methyl-1-oxopentadecan-3-yl) 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate

There total 4 articles about (S)-1-((S)-1-(benzyloxy)-14-methyl-1-oxopentadecan-3-yl) 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate 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: 90.0%

(S)-3-methyl-5-oxo-5-(((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)pentanoic acid (1402050-36-5) + benzyl 3-hydroxy-14-methylpentadecanoate → (S)-1-((S)-1-(benzyloxy)-14-methyl-1-oxopentadecan-3-yl) 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate (1402050-37-6)

Guidance literature:

With dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 5h; enantioselective reaction;

DOI:10.1021/jo301803h DOI:10.1021/jo301803h

Reference yield:

(R)-5-(benzyloxy)-3-methyl-5-oxopentanoic acid (1402050-33-2) → (S)-1-((S)-1-(benzyloxy)-14-methyl-1-oxopentadecan-3-yl) 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate (1402050-37-6)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 5 h / 20 °C

2: 10% Pd/C; hydrogen / ethyl acetate / 8 h / 20 °C

3: dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 5 h / 20 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; 10% Pd/C; hydrogen; triethylamine; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo301803h DOI:10.1021/jo301803h

Reference yield:

(S)-1-benzyl 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate (1402050-34-3) → (S)-1-((S)-1-(benzyloxy)-14-methyl-1-oxopentadecan-3-yl) 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate (1402050-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 10% Pd/C; hydrogen / ethyl acetate / 8 h / 20 °C

2: dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 5 h / 20 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; 10% Pd/C; hydrogen; triethylamine; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo301803h DOI:10.1021/jo301803h

upstream raw materials:

(R)-5-(benzyloxy)-3-methyl-5-oxopentanoic acid

(S)-1-benzyl 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate

(S)-3-methyl-5-oxo-5-(((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)pentanoic acid

3-methylglutaric anhydride