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Stereoselective Synthesis of 2-Deoxyglycosides by Use of 2-Deoxypyranosyl Dithiocarbamates as Donors

Wandzik I., Szeja W.

Polish Journal of Chemistry

1999

vol. 73 nr 7

1163-1170

Glycosides, derivatives of 2-deoxysugars can be conveniently prepared by treatment of glycosyl dithiocarbamates (glycosyl donors) with hydroxy compounds (glycosyl acceptors) in the presence of thiophilic compounds as activators.

The reaction of (methylthio)acetyliron complex with pentose terminal aldehydes

Wiśniewski K., Zamojski A.

Polish Journal of Chemistry

1998

Vol. 72, nr 8

1937-1948

The reaction between anion generated from (methylthio)acetyliron complex (1) and four stereoisomeric dialdo-1,4-furanoses was performed. Each aldehyde led to mixtures (6-8) of stereoisomeric aldols. Aldols were separated and their configaration was determined. Decomplexation of these products was studied with oxidative (NCS, Cl2, I2, CuCl2) and reducing (BH3xMe2S and NaBH4) reagents. Sugar derivatives were isolated and their structures were deduced.