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Unusual C-C Bond Cleavage of an α-trifloxy Sialic Acid Hemiacetal Under Lattrell-Dax Conditions

Overview
Journal Carbohydr Res
Publisher Elsevier
Specialties Biochemistry
Endocrinology
Date 2021 Dec 27
PMID 34959032
Authors
Santanu Jana
David Crich
Affiliations
Soon will be listed here.
Abstract

We describe the novel oxidative fragmentation of methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-trifluoromethanesulfonyl-β-D-erythro-L-gluco-2-nonulopyranos)onate 2 on stirring with sodium nitrite in DMF to give the novel 3-acetamido-2,5,6,7-tetra-O-acetyl-d-glycero-d-galacto-heptono-1,4-lactone 3 in excellent yield. Stirring of the same triflate with sodium carbonate on the other hand affords the novel methyl (5-acetamido-7,8,9-tri-O-acetyl-3,6-anhydro-5-deoxy-d-manno-3-ene-2-nonulos)onate 19 also in excellent yield. Reduction of the heptono lactone with sodium borohydride followed by acetylation gives a peracetylated aminodeoxyheptitol 6 that adopts the zig zag conformation of its carbon backbone.

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