Synthesis and Isolation of Diastereomeric Anomeric Sulfoxides from a d-Mannuronate Thioglycoside Building Block

Abstract

Methyl [S-phenyl 4-O-acetyl-2,3-di-O-benzyl-1-thio-α-d-mannopyranoside (R/S)S-oxide] uronate was synthesised from a thioglycoside mannosyl uronate donor in a 98% yield. By using one equivalent of meta-chloroperbenzoic acid (m-CPBA) as the sulphur oxidant, a smooth conversion to the diastereomeric sulfoxide products was achieved. The product was fully characterized by 1H, 13C and 2D NMR alongside MS analysis.

Editorial: Special Issue “Molecules from Side Reactions”

“…In the seventh paper, an unexpected epoxide-oxetane rearrangement was observed during the synthesis of symmetrical dodeco-6,7-diuloses, that are potential candidates for inhibition of glycosidases [8]. In the eighth paper, a novel glycosyl sulfoxide was synthesized from a S-phenyl thioglycoside for the preparation of alginate oligosaccharides [9]. In the ninth paper, the authors discovered that the incorporation of 8-fluoro-N-2-isobutyryl-2 -deoxyguanosine into oligonucleotides through the phosphoramidite chemistry-based solid phase synthesis failed to give the desired products.…”