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Stereoselective Synthesis of [13C]methyl 2-[15N]amino-2-deoxy-beta-D-glucopyranoside Derivatives

Stereoselective Synthesis of [13C]methyl 2-[15N]amino-2-deoxy-beta-D-glucopyranoside Derivatives

F P Boulineau, A Wei

Carbohydr Res. 2001 Sep 7;334(4):271-9.

PMID: 11527528

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	CAS Number	Price
AP145143017	Boc-Gly-OH-2-13C,15N	145143-01-7	Price
AP285977868	L-Alanine-2-13C,15N	285977-86-8	Price
AP285978247	Glyphosate-2-13C,15N	285978-24-7	Price
IAR42410617	Fmoc-Gly-OH-2-13C,15N		Price

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