Stereoselective synthesis of [ 13C]methyl 2-[ 15N]amino-2-deoxy-β- d-glucopyranoside derivatives

Efficient syntheses of three [ 13C]methyl 2-[ 15N]amino-2-deoxy-β- 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...

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Veröffentlicht in:	Carbohydrate research 2001-09, Vol.334 (4), p.271-279
Hauptverfasser:	Boulineau, Fabien P, Wei, Alexander
Format:	Artikel
Sprache:	eng
Schlagworte:	13C-Labeling 15N-Labeling Carbon Isotopes Deoxyglucose - analogs & derivatives Deoxyglucose - chemistry Glucans - chemical synthesis Heteronuclear coupling constants Hydrocarbons, Iodinated - chemistry Isotope Labeling - methods Methylation Nitrogen Isotopes Nuclear Magnetic Resonance, Biomolecular Stereoisomerism Stereoselectivity Trifluoroacetic Acid - chemistry
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Zusammenfassung:	Efficient syntheses of three [ 13C]methyl 2-[ 15N]amino-2-deoxy-β- 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 β 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. Graphic
ISSN:	0008-6215 1873-426X
DOI:	10.1016/S0008-6215(01)00203-8