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Literature DB >> 25771297

C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates.

Abstract

The iodocyclization of homoallylic trichloroacetimidates derived from α-C-allyl galactoside were investigated. In line with the stereochemical trend observed for less substituted non-glycosylated frameworks, E and Z substrates delivered stereoselectively the 1,3-anti and 1,3-syn amino alcohol motifs, respectively. These products are advanced precursors to C-glycosides of the potent immunostimulatory glycolipid KRN7000.

Entities: CellLine Chemical Disease Gene

Keywords: C-Glycoside; Glycolipid; Glycomimetic; Imidate; Iodocyclization; KRN7000; Oxazine

Mesh：

Substances：

Year: 2015 PMID： 25771297 PMCID： PMC5240635 DOI： 10.1016/j.carres.2015.02.005

Source DB: PubMed Journal: Carbohydr Res ISSN： 0008-6215 Impact factor: 2.104

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References

25 in total

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C-glycosphingolipid precursors via iodocyclization of homoallyic trichloroacetimidates.

1. Inhibition of glycosphingolipid biosynthesis: application to lysosomal storage disorders.

2. Synthesis of beta-C-Glycosides of N-Acetylglucosamine via Keck Allylation Directed by Neighboring Phthalimide Groups.

3. Synthesis of a C-glycoside analogue of β-galactosyl ceramide, a potential HIV-1 entry inhibitor.

4. Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).

5. Synthesis of C-glycoside analogues of α-galactosylceramide via linear allylic C-H oxidation and allyl cyanate to isocyanate rearrangement.

6. Efficient synthesis of alpha-C-galactosyl ceramide immunostimulants: use of ethylene-promoted olefin cross-metathesis.

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