Stereoselective synthesis of [13C]methyl 2-[15N]amino-2-deoxy-beta-D-glucopyranoside derivatives.
Efficient syntheses of three [13C]methyl 2-[15N]amino-2-deoxy-beta-D-glucopyranoside derivatives are described. Amination of the D-glucal with (saltmen)Mn(15N) proceeded with 11:1 stereoselectivity favoring the gluco configuration; subsequent methylation of the [15N]lactol using [13C]iodomethane and silver(I) oxide afforded the doubly labeled beta glucoside in high yield. This compound served as the common precursor for three [13C]methyl 2-[15N]aminoglucosides: (2-[15N]trifluoroacetyl-), (2-[15N]acetyl-), and (2-[15N]azido-). Selected heteronuclear coupling constants are reported.
Boulineau
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Department of Chemistry, Purdue University, 1393 Brown Building, West Lafayette, IN 47907-1393, USA.
Wei
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D002247:Carbon Isotopes; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000737:chemistry; D005936:Glucans / Q000138:chemical synthesis*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D007553:Isotope Labeling / Q000379:methods; D008745:Methylation; D009587:Nitrogen Isotopes; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D014269:Trifluoroacetic Acid / Q000737:chemistry
D002247:Carbon Isotopes; D005936:Glucans; D006847:Hydrocarbons, Iodinated; D009587:Nitrogen Isotopes; C001289:d-glucal; C008763:panose; D003847:Deoxyglucose; C014055:methyl iodide; D014269:Trifluoroacetic Acid