A NEW ACCESS TO ENANTIOMERICALLY PURE DEOXY AMINOHEXOSES - METHYL 4-AMINO-4,6-DIDEOXYGULOPYRANOSIDE AND EPI-TOLYPOSAMINE

Authors
KOSKINEN AMP OTSOMAA LA
Citation
Amp. Koskinen et La. Otsomaa, A NEW ACCESS TO ENANTIOMERICALLY PURE DEOXY AMINOHEXOSES - METHYL 4-AMINO-4,6-DIDEOXYGULOPYRANOSIDE AND EPI-TOLYPOSAMINE, Tetrahedron, 53(18), 1997, pp. 6473-6484
Citations number
31
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
18
Year of publication
1997
Pages
6473 - 6484
Database
ISI
SICI code
0040-4020(1997)53:18<6473:ANATEP>2.0.ZU;2-#
Abstract
New efficient synthetic routes have been developed starting from the f ully protected L-threonine derivative 1 for some deoxy-4-aminohexoses: methyl 4-amino-4,6-dideoxy gulopyranoside 2 and epi-tolyposamine 3. T he title compounds were synthesized using an improved Horner-Emmons re action of the threonine derived aldehyde 7. A new method for selective removal of the aminal protection is also reported. (C) 1997 Elsevier Science Ltd.