Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

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

Similar articles

See all similar articles

Cited by

References

    1. La Ferla B, Airoldi C, Zona C, Orsato A, Cardona F, Merlo S, Sironi E, D'Orazio G, Nicotra F. Nat. Prod. Rep. 2011;28:630–648. - PubMed
    1. Bhattacharya C, Yu Z, Rishel MJ, Hecht SM. Biochemistry. 2014;53:3264–3266. - PMC - PubMed
    1. Wojtkielewicz A, D1ugosz M, Maj J, Morzycki JW, Nowakowski M, Renkiewicz J, Strnad M, Swaczynová J, Wilczewska AZ, Wójcik J. J. Med. Chem. 2007;50:3667–3673. - PubMed
    1. Lorent JH, Quetin-Leclercq J, Mingeot-Leclercq M-P. Org. Biomol. Chem. 2014;12:8803–8022. - PubMed
    1. Shukla RK, Tiwari A. Crit. Rev. Ther. Drug Carrier Syst. 2011;28:255–292. - PubMed

Publication types

LinkOut - more resources