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. 2016 Apr 29:425:43-7.
doi: 10.1016/j.carres.2016.03.002. Epub 2016 Mar 16.

A ring closing metathesis strategy for carbapyranosides of xylose and arabinose

Clayton E Mattis  1 , David R Mootoo  2
Affiliations

A ring closing metathesis strategy for carbapyranosides of xylose and arabinose

Clayton E Mattis et al. Carbohydr Res. .

Abstract

The synthesis of β-carba-xylo and arabino pyranosides of cholestanol is described. The synthetic strategy, which is analogous to the Postema approach to C-glycosides, centers on the ring closing metathesis of an enol ether-alkene precursor to give a cyclic enol ether that is elaborated to a carba-pyranoside via hydroboration-oxidation on the olefin. The method, which is attractive for its modularity and stereoselectivity, may find wider applications to carba-hexopyranosides and other complex cycloalkyl ether frameworks.

Keywords: Arabinose; Carbasugar; Cholestanol (PubChem CID: 6665); Cycloalkyl ether; Dimethyl sulfide borane (PubChem CID: 9833925); Glycomimetic; Grubbs catalyst 2nd generation (PubChem CID: 11147261); Methyl (triphenylphosphoranylidene)acetate (PubChem CID: 17453); Methyl 2,3-O-isopropylidene-beta-d-ribofuranoside (PubChem CID: 96666); Methyl alpha-d-arabinofuranoside (PubChem CID: 11389582); RCM; Tebbe reagent (PubChem CID: 91617563); Xylose.

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Figures

Figure 1
Figure 1
OSW-1 and carbasugar analogues
Scheme 1
Scheme 1
RCM strategies to C- and carba- pyranosides
Scheme 2
Scheme 2
Synthesis of “glycone” precursors
Scheme 3
Scheme 3
Synthesis of carba-3β-cholestanyl pentopyranosides
See this image and copyright information in PMC

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