ISSN:
1434-193X
Keywords:
Sucrose
;
Acetalation
;
Etherification
;
Carbohydrate
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reaction of unprotected sucrose with tert-butyl chloromethyl ketone in dimethylformamide was investigated as a model for the study of the relative reactivity of the various hydroxy groups of sucrose. Besides the monoethers arising from the substitution of the chlorine atom by 2-OH and 1′-OH of sucrose, the major product is a tert-butyl hydroxymethyl 5-membered ring acetal involving 2-OH and 3-OH. The formation of this product illustrates the preeminent reactivity of 2-OH towards the carbonyl group of the α-chloromethyl ketone, leading to an intermediate hemiacetalic anion, which can enter by intramolecular acetal formation through an intermediate epoxide.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
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