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

Base Information

• Chemical Name: (S)-1-benzyl 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate
• CAS No.: 1402050-34-3
• Molecular Formula: C₂₂H₃₂O₈
• Molecular Weight: 424.491
• Mol file: 1402050-34-3.mol

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

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

There total 6 articles about (S)-1-benzyl 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: 70.0%

(3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-ol (14187-51-0) + (R)-5-(benzyloxy)-3-methyl-5-oxopentanoic acid (1402050-33-2) → (S)-1-benzyl 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate (1402050-34-3)

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: 48.0%

(3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-ol (14187-51-0) + C13H15ClO3 → (S)-1-benzyl 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate (1402050-34-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -40 - 25 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.9b02220

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (S)-1-benzyl 5-((2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl) 3-methylpentanedioate (1402050-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1: C₃₄H₂₀N₂Ni₂O₄ / chloroform / 48 h / 0 °C

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

With dmap; 2,4,6-trichlorobenzoyl chloride; C₃₄H₂₀N₂Ni₂O₄; triethylamine; In tetrahydrofuran; chloroform;

DOI:10.1021/jo301803h DOI:10.1021/jo301803h

upstream raw materials:

(3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-ol

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

benzyl alcohol

3-methylglutaric anhydride

Downstream raw materials:

(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