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Synthesis of Acylated Methyl 2-Acetamido-2-Deoxy-alpha-D-Mannopyranosides

2-Acetamido-2-deoxy-betha-D-mannopyranose (1) was glycosylated by the Fischer method using an acidic ion-exchange resin as the catalyst to give alpha-methyl glycoside 2. Selective pivaloylations of methyl 2-acetamido-2-deoxy-alpha-D-mannopyranoside (2) have been studied under various reaction conditions. Two partially pivaloylated products were submitted to additional acetylations. All structures were established by NMR spectroscopy. Structure of the methyl 2-acetamido-2-deoxy-3, 6-di-O-pivaloyl-alpha-D-mannopyranoside (4) was determined by X-ray analysis.

Methyl 2-acetamido-2-deoxy-alpha-D-mannopyranosides; Acyl; Pivaloyl; Acetyl

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