345341-29-9

Upstream product

• 345341-24-4 2,3,7-Tri-O-acetyl-8-bromo-8-deoxy-5,6-O-isopropylidene-D-erythro-L-galacto-octono-1,4-lactone 
• 345341-23-3 8-Bromo-8-deoxy-5,6-O-isopropylidene-D-erythro-L-galacto-octono-1,4-lactone 
• 345341-22-2 8-Bromo-8-deoxy-D-erythro-L-galacto-octono-1,4-lactone 
• 56570-93-5 D-erythro-L-galacto-Octono-1,4-lactone 
• 345341-27-7 (1S,3R,4R,5R,6S,9S)-3,9-Diacetoxy-4,5-isopropylidenedioxy-7-oxabicyclo[4.3.0]nonan-8-one 
• 345341-25-5 2,7-Di-O-acetyl-8-bromo-3,8-dideoxy-5,6-O-isopropylidene-D-gluco-oct-2-enono-1,4-lactone 

Relevant academic research and scientific papers

Synthesis of carba sugars from aldonolactones. Part IV. Stereospecific synthesis of carbaheptopyranoses by radical-induced carbocyclisation of 2,3-unsaturated octonolactones

Three new carbaheptopyranoses, 6-deoxy-5a-carba-β-L-gulo- (8), 5a-carba-D-glycero-β-D-ido- (22) and 5a-carba-Lglycero-α-L-galacto-heptopyranose (25), have been prepared from 8-bromo-8-deoxy-2,3-unsaturated octono-1,4-lactones with L-galacto-, D-gluco- and D-manno-configuration, respectively. The key step was a regio- and stereoselective 6-exo-trig radical-induced carbocyclisation of the unsaturated octonolactones to give bicyclic cyclohexane-lactone derivatives. Reduction of the lactone moiety using Ca(BH4)2 gave the said carbaheptopyranoses. The 8-bromo-8-deoxy-2,3-unsaturated octonolactones were prepared from the inexpensive, commercially available D-glycero-D-gulo-heptonolactone and L-tartaric acid.