179260-97-0

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 621-59-0 isovanillin 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 179260-96-9 4-methoxy-3-(triisopropylsilyloxy)-benzaldehyde 

Downstream Products

• 179260-99-2 Toluene-4-sulfonic acid (S)-2-hydroxy-2-(4-methoxy-3-triisopropylsilanyloxy-phenyl)-ethyl ester 
• 179261-00-8 Triisopropyl-((S)-2-methoxy-5-oxiranyl-phenoxy)-silane 
• 21499-23-0 phyllodulcin 
• 179260-98-1 (S)-1-(4-Methoxy-3-triisopropylsilanyloxy-phenyl)-ethane-1,2-diol 

Relevant academic research and scientific papers

Highly enantioselective synthesis of natural phyllodulcin

(S)-[4-Methoxy-3-[(triisopropylsilyl)oxy]phenyl)oxirane (prepared from isovanillin by consecutive silylation, olefination, Sharpless asymmetric cis-dihydroxylation, and dehydration) reacted with [3-(methoxymethoxy)phenyl]lithium (prepared from 3-bromophenol by consecutive methoxymethylation and bromine-lithium exchange) to yield (R)-1-[4-methoxy-3-[(triisopropylsilyl)oxy]phenyl)2-[3-(methoxymethoxy )phenyl]ethanol. The last compound underwent selective hydrogen-metal exchange with excess of butyllithium affording (after carbonation, lactonization, and deprotection of phenolic groups) the title compound [(R)-3,4-dihydro-8-hydroxy-3-(4-methoxy-3-hydroxyphenyl)isocoumarin].