Synthesis of 2-iodo-2-deoxy septanosides from a D-xylose-based oxepine: intramolecular cyclization in the absence of a glycosyl acceptor.
Oxidative glycosylations of the D-xylose-based oxepine 1,6-anhydro-3,4,5-tri-O-benzyl-2-deoxy-D-xylosept-1-enitol (1) using N-iodosuccinimide (NIS) are reported. The reaction produced 2-deoxy-2-iodo-alpha-D-idoseptanosides and 2-deoxy-2-iodo-beta-D-guloseptanosides 2-9 in good yields. When limited equivalents of a glycosyl acceptor were used, or in the absence of a glycosyl acceptor, an intramolecular cyclization predominated to form 1,6-anhydro-3,4-di-O-benzyl-2-deoxy-2-iodo-alpha-D-idopyranose (10).
Fyvie
W Sean
WS
Department of Chemistry, The University of Connecticut, 55 North Eagleville Road, Storrs, CT 06269, USA.
Morton
Martha
M
Peczuh
Mark W
MW
D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D006601:Hexoses / Q000138:chemical synthesis / Q000737:chemistry; D010082:Oxepins / Q000138:chemical synthesis; D010084:Oxidation-Reduction; D013388:Succinimides / Q000737:chemistry; D014994:Xylose / Q000737:chemistry
C498069:1,6-anhydro-3,4,5-tri-O-benzyl-2-deoxyxylosept-1-enitol; D006027:Glycosides; D006573:Heterocyclic Compounds, 1-Ring; D006601:Hexoses; D010082:Oxepins; D013388:Succinimides; C010997:idose; C008155:N-iodosuccinimide; D014994:Xylose