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An Improved Approach to the Direct Construction of 2-Deoxy-?-Linked Sugars: Applications to Oligosaccharide Synthesis.

ABSTRACT: A next-generation reagent-controlled approach for the synthesis of 2,6-dideoxy and 2,3,6-trideoxy sugar donors in good yield and high ?-selectivity is reported. The use of p-toluenesulfonyl chloride and potassium hexamethyldisilazide (KHMDS) greatly simplifies deoxy-sugar glycoside construction, and can be used for gram-scale glycosylation reactions. The development of this approach and its application to the construction of ?-linked deoxy-sugar oligosaccharides are described.

SUBMITTER: Lloyd D

PROVIDER: S-EPMC6094935 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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An Improved Approach to the Direct Construction of 2-Deoxy-β-Linked Sugars: Applications to Oligosaccharide Synthesis.

Lloyd Dina D Bennett Clay S CS

Chemistry (Weinheim an der Bergstrasse, Germany) 20180502 30

A next-generation reagent-controlled approach for the synthesis of 2,6-dideoxy and 2,3,6-trideoxy sugar donors in good yield and high β-selectivity is reported. The use of p-toluenesulfonyl chloride and potassium hexamethyldisilazide (KHMDS) greatly simplifies deoxy-sugar glycoside construction, and can be used for gram-scale glycosylation reactions. The development of this approach and its application to the construction of β-linked deoxy-sugar oligosaccharides are described. ...[more]

PMID: 29572995

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