One-pot protection-glycosylation reactions for synthesis of lipid II analogues

Katsuhiko Mitachi, Priya Mohan, Shajila Siricilla, Michio Kurosu

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

(2,6-Dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methyl trichloroacetimidate (3) and its polymer-supported reagent 4 can be successfully applied to a one-pot protection-glycosylation reaction to form the disaccharide derivative 7 d for the synthesis of lipid II analogues. The temporary protecting group or linker at the C-6 position and N-Troc protecting group of 7 d can be cleaved simultaneously through a reductive condition. Overall yields of syntheses of lipid II (1) and neryl-lipid II Nε-dansylthiourea are significantly improved by using the described methods. Sweet synthetic methods: A one-pot protection glycosylation reaction of the diol glycosyl acceptor is developed for synthesis of the lipid II disaccharide (see figure, Troc=2,2,2-trichloroethoxycarbonyl). Improved syntheses of lipid II and neryl-lipid II analogues are summarized.

Original languageEnglish (US)
Pages (from-to)4554-4558
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number16
DOIs
StatePublished - Apr 14 2014

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Glycosylation
Lipids
Disaccharides
muramyl-NAc-(pentapeptide)pyrophosphoryl-undecaprenol
Polymers
Derivatives

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

One-pot protection-glycosylation reactions for synthesis of lipid II analogues. / Mitachi, Katsuhiko; Mohan, Priya; Siricilla, Shajila; Kurosu, Michio.

In: Chemistry - A European Journal, Vol. 20, No. 16, 14.04.2014, p. 4554-4558.

Research output: Contribution to journalArticle

Mitachi, Katsuhiko ; Mohan, Priya ; Siricilla, Shajila ; Kurosu, Michio. / One-pot protection-glycosylation reactions for synthesis of lipid II analogues. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 16. pp. 4554-4558.
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