Benzoic acid (1S,3R,4R)-6-benzyloxy-4-hydroxy-1,3-dimethyl-2-oxo-hexyl ester

Base Information

• Chemical Name: Benzoic acid (1S,3R,4R)-6-benzyloxy-4-hydroxy-1,3-dimethyl-2-oxo-hexyl ester
• CAS No.: 332179-83-6
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.445
• Mol file: 332179-83-6.mol

Synonyms:Benzoic acid (1S,3R,4R)-6-benzyloxy-4-hydroxy-1,3-dimethyl-2-oxo-hexyl ester

Chemical Property of Benzoic acid (1S,3R,4R)-6-benzyloxy-4-hydroxy-1,3-dimethyl-2-oxo-hexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,3R,4R)-6-benzyloxy-4-hydroxy-1,3-dimethyl-2-oxo-hexyl ester

There total 1 articles about Benzoic acid (1S,3R,4R)-6-benzyloxy-4-hydroxy-1,3-dimethyl-2-oxo-hexyl 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: 88.0%

3-Benzyloxypropanal (19790-60-4) + (S)-2-benzoyloxypentan-3-one (160666-92-2) → Benzoic acid (1S,3R,4R)-6-benzyloxy-4-hydroxy-1,3-dimethyl-2-oxo-hexyl ester (332179-83-6)

Guidance literature:

(S)-2-benzoyloxypentan-3-one; With N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In diethyl ether; at 0 ℃; for 2h;

3-Benzyloxypropanal; In diethyl ether; at -78 - -20 ℃; for 16h;

With dihydrogen peroxide; In methanol; pH=7;

DOI:10.1016/S0040-4039(00)02205-X

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + Benzoic acid (1S,3R,4R)-6-benzyloxy-4-hydroxy-1,3-dimethyl-2-oxo-hexyl ester (332179-83-6) → Benzoic acid (1S,3R,4R)-6-benzyloxy-1,3-dimethyl-2-oxo-4-triisopropylsilanyloxy-hexyl ester

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃; for 3h;

DOI:10.1016/S0040-4039(00)02205-X

Reference yield:

Benzoic acid (1S,3R,4R)-6-benzyloxy-4-hydroxy-1,3-dimethyl-2-oxo-hexyl ester (332179-83-6) → (2R,3R)-5-Benzyloxy-2-methyl-3-triisopropylsilanyloxy-pentanal (332179-84-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 3 h / -78 - 0 °C

2: LiAlH₄ / 3 h / -78 - 0 °C

3: Pd(OAc)4; Na₂CO₃ / CH₂Cl₂ / 0.5 h

With palladium(II) acetate; 2,6-dimethylpyridine; lithium aluminium tetrahydride; sodium carbonate; In dichloromethane;

DOI:10.1016/S0040-4039(00)02205-X

upstream raw materials:

3-Benzyloxypropanal

(S)-2-benzoyloxypentan-3-one

Downstream raw materials:

(2R,3R)-5-Benzyloxy-2-methyl-3-triisopropylsilanyloxy-pentanal

(E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one