Stereoselective synthesis of the alpha-allyl C-glycoside of 3-deoxy-D-manno-2-octulosonic acid (KDO) by use of radical chemistry.
Methyl 2-C-allyl-2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero- D-talo-octonate (9a), the protected alpha-allyl C-glycoside of 3-deoxy-D-manno-2-octulosonic acid (KDO), has been synthesized using a photochemically initiated radical reaction. A phenyl thioglycoside (8) was used as the substrate and allyltributyltin as the acceptor. The stereoselectivity of the reaction was 90:10 in favour of the talo-isomer (alpha-).
Wåglund
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Department of Organic Pharmaceutical Chemistry, Uppsala Biomedical Center, University of Uppsala, Sweden.
Claesson
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A
D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry; D005609:Free Radicals; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010777:Photochemistry; D013237:Stereoisomerism; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry
D000890:Anti-Infective Agents; D005609:Free Radicals; D013400:Sugar Acids