307492-80-4

Upstream product

• 25458-46-2 4-methoxyphenyl methoxymethyl ether 
• 150-76-5 4-methoxy-phenol 
• 434928-87-7 (E)-2-(4-hydroxy-3-methylbut-3-en-1-yl)-4-methoxy-1-methoxymethoxybenzene 
• 307492-77-9 4-methoxy-1-(methoxymethoxy)-2-(3-methylbut-2-en-1-yl)benzene 
• 307492-79-1 (2R,3R)-2-(2,3-epoxy-4-hydroxy-3-methylbutyl)-4-methoxy-1-methoxymethoxybenzene 

Downstream Products

• 307492-81-5 (S)-(+)-2-[2-(2,2,4-trimethyl-1,3-dioxolan-4-yl)ethyl]-4-methoxy-1-(methoxymethox)ybenzene 
• 307492-87-1 (2S)-(+)-4-bromo-2-methyl-6-tosyloxy-2-tosyloxymethyl-2H-chromene 
• 307492-90-6 C₂₅H₂₅BrO₇S₂ 
• 307492-86-0 C₂₅H₂₆O₇S₂ 
• 307492-88-2 (2S)-(+)-2-methyl-6-tosyloxy-2-(tosyloxymethyl)-2H-chromene 
• 307492-89-3 toluene-4-sulfonic acid 2-methyl-2-(4-methyl-pent-3-enyl)-2H-chromen-6-yl ester 

Relevant academic research and scientific papers

Asymmetric syntheses of daedalin A and quercinol and their tyrosinase inhibitory activity

Stereoselective syntheses of daedalin A and quercinol, an enantiomer of daedalin A, is described. The tyrosinase inhibitory activities of daedalin A and quercinol were examined. The activity of quercinol was weaker than that of daedalin A at high concentration.

A useful enantioselective synthesis of chroman-2-ylmethanol

An enantioselective synthesis of chromanylmethanol is described. An allylic alcohol moiety is, first, introduced on the aromatic ring through a Claisen transposition. Chirality is then introduced through asymmetric Sharpless epoxidation on the allylic alcohol moiety. Cyclization into the benzopyran ring is achieved by an intramolecular coupling between the tertiary alcoholic hydroxy and the hydroquinone moiety with an excellent retention of configuration.

Enantioselective synthesis of cordiachromene

An enantioselective synthesis of cordiachromene is described. An allylic alcohol moiety is first attached in the o-position to the methoxymethoxy substituent in 1-methoxy-4-methoxymethoxybenzene. Then chirality is introduced successively through asymmetric Sharpless epoxidation on the allylic alcohol moiety and regioselective ring-opening. The chiral diol prepared is then cyclized to chromanmethanol with total retention of configuration. Chromenemethanol is obtained after bromination and dehydrobromination. The total synthesis is achieved by reaction between the tosylated chromene chiral moiety and an organomagnesium prenylated compound.