482580-65-4

Upstream product

• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 357204-56-9 3-nitro-O-benzyl-1-propanol 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 482580-35-8 1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-trityloxy-butan-2-one 
• 482580-33-6 4-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-2-one 
• 482580-51-8 (S)-4-((Z)-4-Benzyloxy-2-nitro-but-1-enyl)-2,2-dimethyl-[1,3]dioxolane 

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.