Stereoselective synthesis of 2-deoxyglycosides from sulfanyl alkenes by consecutive "one pot" cyclization and glycosylation reactions

Identifier:  imarina:9284607

Handle: https://hdl.handle.net/20.500.11797/imarina9284607

Authors:  Rodríguez, MA; Boutureira, O; Matheu, MI; Díaz, Y; Castillón, S

Abstract:
2-Deoxy-2-iodopyranosides 3, and 9-12 were synthesized from sulfanyl alkenes using a "one pot" consecutive cyclization-glycosylation process. Compared with the stepwise procedure, the "one pot" process gave significantly improved yields with similar or slightly lower selectivities. The "one pot" procedure was applied to the synthesis of 2,6-dideoxy-2-iodoglycoside 22, which was successfully deiodinated to afford the 2,6-dideoxyglycoside 23. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.