853750-36-4

Upstream product

• 853750-14-8 (4R)-4-benzyl-3-{(2R)-2-[(R)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 155399-10-3 (4R)-3-(4-pentenoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one 

Downstream Products

• 853750-38-6 (S)-2-[(R)-(3,4-dimethoxyphenyl)(triethylsilyloxy)methyl]-4-penten-1-ol 
• 853750-40-0 (S)-3-[(R)-(3,4-dimethoxyphenyl)(triethylsilyloxy)methyl]-4-butanolide 
• 853750-28-4 (1S,2R,3R)-2,3-bis[(tert-butyldiphenylsilyloxy)methyl]-1-(3,4-dimethoxyphenyl)-3-(3,4-methylenedioxybenzoyl)-1-(triethylsilyloxy)propane 

Relevant academic research and scientific papers

Syntheses and antimicrobial activity of tetrasubstituted tetrahydrofuran lignan stereoisomers

The syntheses of all stereoisomers of tetrasubstituted tetrahydrofuran lignan were accomplished, and the antimicrobial activity was examined. The 9, 9′-diol compound bearing (7R, 7′R, 8R, 8′R) and (7R, 7′S, 8R, 8′R) stereochemistry showed the strongest antibacterial activity against Listeria denitrificans and Bacillus subtilis, respectively. It was also found that ()-virgatusin bearing (7S, 7′R, 8S, 8′S) stereochemistry had strongest antifungal activity.

First enantioselective synthesis of (-)- And (+)-virgatusin, tetra-substituted tetrahydrofuran lignan

The first highly enantioselective syntheses of tetra-substituted tetrahydrofuran lignan, (-)- and (+)-virgatusin, were achieved. Hemiacetal 15 was stereoselectively obtained from Evans's syn-aldol product 8 as a single isomer. This hemiacetal 15 was converted to (-)-virgatusin via hydrogenolysis. (+)-Virgatusin was also synthesized through the same process. The enantiomeric excess of the both enantiomers was determined as more than 99% ee. The Royal Society of Chemistry 2005.