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Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach.

ABSTRACT: The synthesis of the hexasaccharide fragment of landomycin A is reported. Using p-toluenesulfonyl chloride mediated dehydrative glycosylation, we constructed the deoxy-sugar linkages in a stereoselective fashion without the need for temporary prosthetic groups to control selectivity. Through this approach, the hexasaccharide was obtained in 28 steps and 8.9% overall yield, which is an order of magnitude higher than that of previously reported approaches.

SUBMITTER: Yalamanchili S

PROVIDER: S-EPMC6746318 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Synthesis of the Hexasaccharide Fragment of Landomycin A Using a Mild, Reagent-Controlled Approach.

Yalamanchili Subbarao S Lloyd Dina D Bennett Clay S CS

Organic letters 20190425 10

The synthesis of the hexasaccharide fragment of landomycin A is reported. Using p-toluenesulfonyl chloride mediated dehydrative glycosylation, we constructed the deoxy-sugar linkages in a stereoselective fashion without the need for temporary prosthetic groups to control selectivity. Through this approach, the hexasaccharide was obtained in 28 steps and 8.9% overall yield, which is an order of magnitude higher than that of previously reported approaches. ...[more]

PMID: 31021647

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