An intramolecular 1,3-dipolar cycloaddition reaction towards the synthesis of chiral azetidine nucleoside analogues: the D-gluco case.
The diastereoselective intramolecular 1,3-dipolar cycloaddition reaction of unsaturated nitrones, derived from methyl alpha-D-glucopyranoside with 2-furaldehyde and 2-(benzyloxy)acetaldehyde has been studied In our pevious studies with 2-furaldehyde, the cycloaddition resulted 3 diastereoisomers in a 3:1:1 ratio. In this article, how the number of the possible isomers generated by 1,3-cycloaddition could be reduced from 4 to 1 when 2-(benzyloxy)acetaldehyde was employed as an aldehyde is shown.
Pádár
P
P
Department of Medicinal Chemistry, Heriot-Watt University, Riccarton, Edinburgh, UK.
Forgó
P
P
Kele
Z
Z
Howarth
N M
NM
Kovács
L
L
D000447:Aldehydes / Q000737:chemistry; D001384:Azetidines / Q000737:chemistry*; D002384:Catalysis; D003035:Cobalt / Q000737:chemistry; D005662:Furaldehyde / Q000737:chemistry; D008956:Models, Chemical; D008967:Molecular Biology / Q000379:methods; D008968:Molecular Conformation; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D000447:Aldehydes; D001384:Azetidines; D009589:Nitrogen Oxides; D009705:Nucleosides; D012997:Solvents; C015388:nitrones; C082735:azetidine; D003035:Cobalt; D005662:Furaldehyde; D015032:Zinc