848862-07-7

Upstream product

• 98-88-4 benzoyl chloride 
• 281678-19-1 methyl 5-deoxy-5-iodo-D-arabinofuranoside 

Downstream Products

• 1201913-23-6 (2R,3S,4R)-3,4-bis(O-benzoyl)-1,1-difluoro-1-phenylselanyl-hex-5-ene-2,3,4-triol 
• 284031-44-3 (3R,4R,5S)-3,4,5-trihydroxyazepane 
• 848862-09-9 (3R,4S,5S)-3,4-dibenzoyloxy-8-oxa-1-azabicyclo[3.2.1]octane 

Relevant academic research and scientific papers

Synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses: en route to fluorinated carbanucleosides

The synthesis of difluorinated carbocyclic analogues of 5-deoxypentofuranoses and 1-amino-5-deoxypentofuranoses is described. The sequence involves an addition of PhSeCF2TMS to carbohydrate-derived aldehydes or their corresponding tert-butanesulfinylimines followed by a radical cyclization. Optimized conditions for the PhSeCF2TMS addition to α-chiral aldehydes have been disclosed and its unusual diastereoselectivity is discussed. Application of the sequence using Ellman's auxiliary allows a more direct access to 1-aminopentose analogues with a complete control of the pseudo-anomeric center configuration.