Conditions for neighboring-group participation in displacement reactions of 5- O-sulfonyl- d-glucofuranose derivatives

Sulfonate displacement reactions of 6- O-benzoyl-1,2- O-isopropylidene-5- O- p-tolylsulfonyl-α- d-glucofuranose derivatives with acetate or chloride ions in acetic anhydride are shown to involve participation by the neighboring benzoyloxy group. Acetate displacement in N,N-dimethylformamide appears...

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Bibliographic Details
Published in:Carbohydrate research 1971-11, Vol.20 (1), p.151-164
Main Authors: Chalk, R.C., Ball, D.H., Long, L.
Format: Article
Language:English
Subjects:
Acetals
Acetates
Anhydrides
Azides
Benzoates
Benzyl Compounds
Chemical Phenomena
Chemistry
Chlorides
Chromatography, Ion Exchange
Dimethylformamide
Furans
Glucose
Phosphoric Acids
Pyrrolidinones
Sulfonic Acids
Tosyl Compounds
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Summary:Sulfonate displacement reactions of 6- O-benzoyl-1,2- O-isopropylidene-5- O- p-tolylsulfonyl-α- d-glucofuranose derivatives with acetate or chloride ions in acetic anhydride are shown to involve participation by the neighboring benzoyloxy group. Acetate displacement in N,N-dimethylformamide appears to occur by both this and the S n2 mechanism, but, with sodium azide in hexamethylphosphoramide, only the S n2 displacement product was formed. Benzylidenation of 1,2- O-isopropylidene-β- l-idofuranose gave the 3,5- O-benzylidene derivative, and the reaction of this acetal with N-bromosuccinimide gave exclusively 5- O-benzoyl-6-bromo-6-deoxy-1,2- O-isopropylidene-β- l-idofuranose.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(00)84957-5