DISPIROKETALS IN SYNTHESIS .17. REGIOSELECTIVE PROTECTION OF D-GLUCOPYRANOSIDE, D-GALACTOPYRANOSIDE AND D-MANNOPYRANOSIDE SUBSTRATES

Authors
EDWARDS PJ ENTWISTLE DA GENICOT C LEY SV VISENTIN G
Citation
Pj. Edwards et al., DISPIROKETALS IN SYNTHESIS .17. REGIOSELECTIVE PROTECTION OF D-GLUCOPYRANOSIDE, D-GALACTOPYRANOSIDE AND D-MANNOPYRANOSIDE SUBSTRATES, Tetrahedron : asymmetry, 5(12), 1994, pp. 2609-2632
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
12
Year of publication
1994
Pages
2609 - 2632
Database
ISI
SICI code
0957-4166(1994)5:12<2609:DIS.RP>2.0.ZU;2-T
Abstract
Chiral recognition of enantiomeric trans-1,2-diol relationships leadin g to regioselective formation of 1,8,13,16-tetraoxadispiro[5.0.5.4] he xadecanes (dispiroketals) of various D-glucopyranoside, D-galactopyran oside and D-mannopyranoside substrates is described. Regioselectivity is achieved using the enantiomerically pure disubstituted tetrahydro-6 ,6'-bi-2H-pyrans 1, 2, 3, 4 and 5. Facile removal of the dispiroketal protecting group from a number of the sugar adducts has been achieved.