19422-99-2

Upstream product

• 4933-77-1 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde 
• 121336-18-3 1,2:3,4-di-O-isopropylidene-6-O-trifluoromethylsulfonyl-α-D-glycero-D-galacto-heptopyranurononitrile 
• 100-46-9 benzylamine 
• 143-33-9 sodium cyanide 

Relevant academic research and scientific papers

STEREOCHEMICAL STUDIES OF THE SYNTHESIS OF α-AMINONITRILES RELATED TO LINCOSAMINE

The syntheses of 6-amino-6-deoxyheptopyranurononitriles related to lincosamine by cyano-amination of 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose (2) is reported.The procedure described allowed direct cyano-amination in good yield under mild conditions.The high diastereofacial selectivity of the reaction is discussed.Indirect cyano-amination by activation of the corresponding cyanohydrins followed by displacement with an amine was also studied.Epimerization occured at C-6 and the resulting aminonitriles were formed under thermodynamic control.From these chain extensions, precursors of lincosamine and analogues were obtained.