1054641-80-3

Upstream product

• 100-39-0 benzyl bromide 
• 482580-45-0 (S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-triisopropylsilanyloxy-butan-2-ol 
• 482580-36-9 1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-triisopropylsilanyloxy-butan-2-one 
• 482580-63-2 (S)-2-benzyl-4-{[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1,3-dioxane 

Downstream Products

• 482580-64-3 (4R,6S)-4-benzyloxy-6-hydroxymethyltetrahydro-2-pyrone 

Relevant academic research and scientific papers

Chelation-controlled reduction: stereoselective formation of syn-1,3-diols and synthesis of compactin and mevinolin lactone.

Chelation-controlled reduction of chiral beta-alkoxy ketones containing a competing beta'-oxygen functionality has been investigated. Various syn-1,3-diols were prepared conveniently by reduction of beta-alkoxy ketones with LiI/LiAlH(4) (syn:anti selectivity up to >99:1). The corresponding beta-alkoxy ketones were derived from nitro-aldol reactions of chiral alkoxy aldehydes with a series of nitro compounds. This methodology is utilized in a short and efficient synthesis of the delta-lactone moiety of the HMG-CoA reductase inhibitors compactin and mevinolin.