Jump to main content
Jump to site search
PLANNED MAINTENANCE Close the message box

Scheduled maintenance work on Wednesday 27th March 2019 from 11:00 AM to 1:00 PM (GMT).

During this time our website performance may be temporarily affected. We apologise for any inconvenience this might cause and thank you for your patience.

Issue 5, 1997
Previous Article Next Article

Nitrile oxide/isoxazoline approach to higher monosaccharides: synthesisof 7-deoxy-nonose and -decosederivatives 1


7-Deoxy-D-ribo-D-galacto - and 7-deoxy-D-xylo-D-galacto-decopy ranoside derivatives 11 and 12 have been prepared by a sequence involving diastereoselective cycloaddition of 2,3-O-isopropylidene-D-glyceronitrile oxide to D-galactose-derived alkene 3 to afford the isoxazoline 5 as the major adduct, followed by reductive hydrolytic cleavage of the isoxazoline and reduction of the resulting β-hydroxy ketone. The configuration of the new chiral centre (C-8) in compounds 11 and 12 is established by NMR analysis of their 6,8-O-isopropylidene derivatives 13 and 14. 7-Deoxy-L-threo-D-galacto- and 7-deoxy-D-erythro-D-galacto-non opyranosides 15 and 16 are prepared similarly from alkene 3 and ethoxycarbonylformonitrile oxide via isoxazolines 8 and 17, and β-hydroxy ketone 18. The 6,7-dideoxynon-6-enos-8-ulose 19 is also prepared from isoxazoline 5.

Back to tab navigation

Article type: Paper
DOI: 10.1039/A606093E
Citation: J. Chem. Soc., Perkin Trans. 1, 1997,0, 629-636

  •   Request permissions

    Nitrile oxide/isoxazoline approach to higher monosaccharides: synthesis of 7-deoxy-nonose and -decose derivatives 1

    R. Michael Paton and A. A. Young, J. Chem. Soc., Perkin Trans. 1, 1997, 0, 629
    DOI: 10.1039/A606093E

Search articles by author