(2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-dihydroxy-4-butanolide

Base Information

• Chemical Name: (2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-dihydroxy-4-butanolide
• CAS No.: 795274-58-7
• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.402
• Mol file: 795274-58-7.mol

Synonyms:(2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-dihydroxy-4-butanolide

Chemical Property of (2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-dihydroxy-4-butanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-dihydroxy-4-butanolide

There total 1 articles about (2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-dihydroxy-4-butanolide 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:

[(2S,3S,4S)-4-((R)-1-Benzyloxy-propyl)-3,4,5-trihydroxy-tetrahydro-furan-2-yl]-phenyl-methanone → (2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-dihydroxy-4-butanolide (795274-58-7)

Guidance literature:

With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; [18F]fluoride ion, cyclotron produced, NCA; In acetonitrile; at 100 ℃; for 0.5h;

DOI:10.1002/jlcr.823

Reference yield: 91.0%

(2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-dihydroxy-4-butanolide (795274-58-7) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-3-hydroxy-2-triethylsiloxy-4-butanolide (795274-59-8)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1246/bcsj.77.1703

Reference yield:

(2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-2,3-dihydroxy-4-butanolide (795274-58-7) → (2S,3S,4S)-4-benzoyl-3-hydroxy-2-(1-propanoyl)-2-triethylsiloxy-4-butanolide (795274-60-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / pyridine / 2 h / 20 °C

2: H₂ / Pd/C / ethyl acetate / 72 h

3: 194 mg / 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide / dimethylsulfoxide / 23 h / 20 °C

With pyridine; hydrogen; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In dimethyl sulfoxide; ethyl acetate;

DOI:10.1246/bcsj.77.1703

Downstream raw materials:

(2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-3-hydroxy-2-triethylsiloxy-4-butanolide

(2S,3S,4S)-4-benzoyl-3-hydroxy-2-(1-propanoyl)-2-triethylsiloxy-4-butanolide