A one-pot synthesis of novel N,N-dialkyl-S-glycosylsulfenamides

Authors
Owen, DJ von Itzstein, M
Citation
Dj. Owen et M. Von Itzstein, A one-pot synthesis of novel N,N-dialkyl-S-glycosylsulfenamides, CARBOHY RES, 328(3), 2000, pp. 287-292
Citations number
12
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
CARBOHYDRATE RESEARCH
ISSN journal
00086215 → ACNP
Volume
328
Issue
3
Year of publication
2000
Pages
287 - 292
Database
ISI
SICI code
0008-6215(20000922)328:3<287:AOSONN>2.0.ZU;2-E
Abstract
An efficient new entry into N,N-dialkyl-S-glycosylsulfenamides is reported. The reaction of bis-activated alkyl halides in the presence of a secondary amine base with glycosylic S-acetyl derivatives (1-S-acetyl-1-thioaldoses or 2-S-acetyl-2-thioketoses) results in the formation of novel carbohydrate sulfenamides. These new carbohydrate-based sulfenamides may provide useful derivatives with biological activity, as well as provide reactive carbohyd rate sulfenylating agents. (C) 2000 Elsevier Science Ltd. All rights reserv ed.