Aldol reactions on 1-deoxy-3,4:5,6-di-O-isopropylidene-L-fructose as a route to higher-carbon carbohydrates.
With a view to preparing higher-carbon carbohydrates, crossed-aldol reactions of the methyl ketone 1-deoxy-3,4:5,6-di-O-isopropylidene-L-fructose with a representative series of aldehydes have been investigated, and the feasibility has been demonstrated of constructing a C-11 unit containing some of the key functionality found in the carbohydrate component of the herbicidins.
Haines
A H
AH
School of Chemical Sciences, University of East Anglia, Norwich, UK. a.haines@uea.ac.uk
Lamb
A J
AJ
D000447:Aldehydes / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D005632:Fructose / Q000031:analogs & derivatives* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D011684:Purine Nucleosides / Q000737:chemistry
C415347:1-deoxy-3,4 5,6-di-O-isopropylidenefructose; D000447:Aldehydes; D002241:Carbohydrates; D007659:Ketones; D011684:Purine Nucleosides; D005632:Fructose; C013551:herbicidins; C116609:3-hydroxybutanal