Application of oxone immobilized on montmorillonite for an efficient oxidation of mannose thioglycoside

Poláková, Monika; Jankovič, Ľuboš; Kucková, Lenka; Kožı́šek, Jozef

doi:10.1007/s00706-013-0964-0

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2020

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“…Glycosyl sulfoxides are traditionally formed by the careful oxidation of a parent thioglycoside component to form an S-oxide, typically by using meta-chloroperbenzoic acid (m-CPBA) as the oxidant, although other methods, including OXONE ® , have recently been developed [3,4]. Whilst the oxidation generally proceeds to yield diastereomeric mixtures, stereoselective sulfoxidations have been reported for particular classes of parent thioglycosides, e.g., α-mannopyranose thioglycosides [5][6][7].…”

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confidence: 99%

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

Dimitriou

Miller

2020

Molbank

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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.

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