Synthesis of CH 2 -Linked α(1,6)-Disaccharide Analogues by α-Selective Radical Coupling C-Glycosylation

Noriaki Kiya, Yu Hidaka, Kazuteru Usui, Go Hirai

Research output: Contribution to journalArticle

Abstract

C-Linked carbohydrate structure, in which the cleavable O-glycosidic linkage is replaced by a carbon unit, is a useful tool for functional analyses of glycoconjugates. We describe a synthetic method for α-CH 2 -linked disaccharide structures, such as Glc(1,6)-Glc, by stereoselective radical-coupling C-glycosylation between a conformationally constrained and stable C1-sp 3 hybridized xanthate donor and a carefully designed acceptor.

Original languageEnglish
Pages (from-to)1588-1592
Number of pages5
JournalOrganic Letters
Volume21
Issue number6
DOIs
Publication statusPublished - Mar 15 2019

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Glycosylation
Glycoconjugates
Disaccharides
carbohydrates
linkages
Carbon
Carbohydrates
methylidyne
analogs
carbon
synthesis

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Synthesis of CH 2 -Linked α(1,6)-Disaccharide Analogues by α-Selective Radical Coupling C-Glycosylation . / Kiya, Noriaki; Hidaka, Yu; Usui, Kazuteru; Hirai, Go.

In: Organic Letters, Vol. 21, No. 6, 15.03.2019, p. 1588-1592.

Research output: Contribution to journalArticle

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