Diastereoselective free-radical synthesis of alpha-substituted C-glycosyl phosphonates, and their use as building blocks in the HWE-reaction

Authors
Junker, HD Phung, N Fessner, WD
Citation
Hd. Junker et al., Diastereoselective free-radical synthesis of alpha-substituted C-glycosyl phosphonates, and their use as building blocks in the HWE-reaction, TETRAHEDR L, 40(39), 1999, pp. 7063-7066
Citations number
15
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
39
Year of publication
1999
Pages
7063 - 7066
Database
ISI
SICI code
0040-4039(19990924)40:39<7063:DFSOAC>2.0.ZU;2-6
Abstract
C-Glycosidic phosphonates were synthesized by the addition of pyranosidic a nd furanosidic glycosyl radicals to alpha-phosphonoacrylates which occurred with high diastereoselectivity towards the formation of alpha-C-glycosidic phosphonates. The products are useful substrates for the synthesis of comp lex higher-carbon sugars related to tunicamycin by Horner-Wadsworth-Emmons reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.