A Mild Procedure for Cleavage of 1,6-Anhydro Sugars
Acetolysis of 1,6-anhydro sugars can be achieved by treatment with acetic anhydride and triethylsilyl trifluoromethanesulphonate at 0 deg C for 5-15 minutes, under which conditions a wide variety of protecting groups are unaffected, and even the trisulphonate is cleaved, albeit in six hours.
Zottola, Mark,Rao, B. Venkateswara,Fraser-Reid, Bert
p. 969 - 970
(2007/10/02)
Photobromination of Carbohydrate Derivatives. VI. Funcionalization at C6 of 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucopyranose
Photobromination of 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-glucopyranose gives the syrupy 6S (exo) bromide in high yield; further reaction leads to secondary bromination at this position.The monobromide reacts with methanol and thiophenol under conditions of kinetic control to give mainly the endo-methoxy and phenylthio derivatives formed by direct nucleophilic displacement, and from the latter the exo-methoxy acetal was obtained by a second nucleophilic substitution.Acetolysis of these compounds can lead to the coresponding exo-6-acetoxy ester or monocyclicproducts formed by opening of the five-membered rings.
Ferrier, Robert J.,Furneaux, Richard H.
p. 1025 - 1036
(2007/10/02)
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