64487-91-8

Upstream product

• 91738-34-0 (3aS,6R,6aS)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3a-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-ol 
• 87-79-6 L-sorbose 
• 143-33-9 sodium cyanide 
• 67-64-1 acetone 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-L-gulonolactone 
• 7757-38-2 2,3:5,6-di-O-isopropylidene-D-mannofuranose 

Relevant academic research and scientific papers

Kiliani on ketoses: Branched carbohydrate building blocks from D-fructose and L-sorbose

Protected branched sugar lactones are available via Kiliani-acetonation sequences on readily available ketoses such as d-fructose and l-sorbose. In both cases, the readily crystallized diacetonides have a 2,3-cis-diol relationship in the product lactone. An efficient double inversion of the configuration at C-4 and C-5 of the product from d-fructose gives access to the formal Kiliani product from l-psicose. Branched carbohydrate lactones are likely to be of significant value as chirons for homochiral targets with functionalized quaternary centres.