Stereoselective synthesis of [C]methyl 2-[N]amino-2-deoxy- -D-glucopyranoside derivatives
نویسندگان
چکیده
Efficient syntheses of three [C]methyl 2-[N]amino-2-deoxy-D-glucopyranoside derivatives are described. Amination of the D-glucal with (saltmen)Mn(N) proceeded with 11:1 stereoselectivity favoring the gluco configuration; subsequent methylation of the [N]lactol using [C]iodomethane and silver(I) oxide afforded the doubly labeled glucoside in high yield. This compound served as the common precursor for three [C]methyl 2[N]aminoglucosides: (2-[N]trifluoroacetyl-), (2-[N]acetyl-), and (2-[N]azido-). Selected heteronuclear coupling constants are reported. © 2001 Elsevier Science Ltd. All rights reserved.
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تاریخ انتشار 2001