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

Authors
Boulineau, FP Wei, A
Citation
Fp. Boulineau et A. Wei, Stereoselective synthesis of [C-13]methyl 2-[N-15]amino-2-deoxy-beta-D-glucopyranoside derivatives, CARBOHY RES, 334(4), 2001, pp. 271-279
Citations number
15
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
CARBOHYDRATE RESEARCH
ISSN journal
00086215 → ACNP
Volume
334
Issue
4
Year of publication
2001
Pages
271 - 279
Database
ISI
SICI code
0008-6215(20010907)334:4<271:SSO[2>2.0.ZU;2-8
Abstract
Efficient syntheses of three [C-13]methyl 2-[N-15]amino-2-deoxy-beta -D-glu copyranoside derivatives are described. Amination of the D-glucal with (sal tmen)Mn(N-15) proceeded with 11:1 stereoselectivity favoring the gluco conf iguration subsequent methylation of the [N-15]lactol using [C-13]iodomethan e and silver(I) oxide afforded the doubly labeled beta glucoside in high yi eld. This compound served as the common precursor for three [C-13]methyl 2- [N-15]aminoglucosides: (2-[N-15]trifluoroacetyl-), (2-[N-15]acetyl-), and ( 2-[N-15]azido-). Selected heteronuclear coupling constants are reported. (C ) 2001 Elsevier Science Ltd. All rights reserved.