1233949-19-3

Upstream product

• 868761-01-7 [difluoro(phenylseleno)methyl]trimethylsilane 

Downstream Products

• 1233949-23-9 (S(S),2S,3R,4R,5R)-3,4-bis(benzyloxy)-2-tert-butanesulfinamido-1,1-difluoro-5-methylcyclopentane 
• 1233949-21-7 (2R,3R,4R)-3,4-bis(benzyloxy)-1,1-difluoro-1-phenylselanyl-2-acetylamino-hex-5-ene 

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.