853786-34-2

Upstream product

• 179122-39-5 (E)-3-(3,5-dimethoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-ol 
• 134-96-3 syringic aldehyde 
• 55211-66-0 3,5-dimethoxy-4-(methoxymethoxy)benzaldehyde 
• 853786-20-6 ethyl (E)-3,5-dimethoxy-4-(methoxymethoxy)-cinnamate 
• 853786-31-9 (1S,2S)-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2,3-dihydroxypropanol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 853786-30-8 (2S,3S)-6-[(E)-2-(3,5-Bis-methoxymethoxy-phenyl)-vinyl]-3-(3,5-dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine 
• 853786-36-4 (1'R,2'S)-4-benzyloxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde 
• 853786-29-5 (2S,3S)-3-(3,5-Dimethoxy-4-methoxymethoxy-phenyl)-2-methoxymethoxymethyl-2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde 
• 853786-38-6 (2R,3R)-3-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde 
• 853786-28-4 (2S,3S)-3-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)-2-hydroxymethyl-2,3-dihydro-1,4-benzodioxin-6-carbaldehyde 
• 853786-37-5 (1'R,2'S)-4-hydroxy-3-[2',3'-epoxy-1'-(3'',5''-dimethoxy-4''-methoxymethoxyphenyl)-propoxy]-benzaldehyde 
• 853786-35-3 (1S,2S)-2,3-epoxy-1-(3',5'-dimethoxy-4'-methoxymethoxyphenyl)propanol 

Relevant academic research and scientific papers

An enantioselective total synthesis of the stilbenolignan (-)-aiphanol and the determination of its absolute stereochemistry

The title natural product (-)-aiphanol has been prepared by total synthesis. A key step involved the asymmetric dihydroxylation of (E)-3,5-dimethoxy-4-(methoxymethoxy)cinnamyl alcohol with the AD-mix-β to give triol (1R,2R)-1-(3′,5′-dimethoxy-4′-methoxymethoxyphenyl) -2,3-dihydroxypropanol, the absolute stereochemistry of which was confirmed by single-crystal X-ray analysis of a readily available bromo-derivative. These studies have established that the naturally occurring enantiomer of aiphanol possesses the (S)-configuration at each of C-2′ and C-3′.