Synthesis and Structural Characterisation of Some Carbohydrate Steroid Hybrids

Glycosteroids are a wide family of natural and synthetic compounds with interesting and diverse architectures. Among synthetic types, we report the synthesis of some monocatenar carbohydrate steroid hybrids connected by a spacer. The strategy is based on the use of the carboxymethylglycosyl lactone strategy towards allyl amides and their connection to an allylated steroid using a cross-metathesis reaction. The scope of the reaction included glucose, galactose and cellobiose, on the carbohydrate side, and to dihydrocholesterol on the steroid side. A series of variously protected new monocatenar synthetic glycosteroids are described.

Automated summary

Glycosteroids, including synthetic monocatenar carbohydrate steroid hybrids, have been synthesized by connecting carboxymethylglycosyl lactone-based allyl amides with allylated steroids through cross-metathesis reaction. The reaction successfully utilized glucose, galactose, cellobiose, and dihydrocholesterol as substrates, resulting in the synthesis of variously protected new glycosteroids.