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

Base Information

• Chemical Name: (2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-3-hydroxy-2-triethylsiloxy-4-butanolide
• CAS No.: 795274-59-8
• Molecular Formula: C₂₇H₃₆O₆Si
• Molecular Weight: 484.665
• Mol file: 795274-59-8.mol

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

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

There total 2 articles about (2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-3-hydroxy-2-triethylsiloxy-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: 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-((R)-1-Benzyloxy-propyl)-3,4,5-trihydroxy-tetrahydro-furan-2-yl]-phenyl-methanone → (2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-3-hydroxy-2-triethylsiloxy-4-butanolide (795274-59-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 352 mg / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 48 h / 20 °C

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

With pyridine; N-iodo-succinimide; tetra-(n-butyl)ammonium iodide; In dichloromethane;

DOI:10.1246/bcsj.77.1703

Reference yield:

(2S,3S,4S)-4-benzoyl-2-[(1R)-1-(benzyloxy)propyl]-3-hydroxy-2-triethylsiloxy-4-butanolide (795274-59-8) → (3R,4S,5R)-4-Hydroxy-5-(hydroxy-phenyl-methyl)-3-((R)-1-hydroxy-propyl)-3-triethylsilanyloxy-dihydro-furan-2-one

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 72h;

DOI:10.1246/bcsj.77.1703

upstream raw materials:

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

triethylsilyl trifluoromethyl sulfonate

Downstream raw materials:

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