Selectivity in removal of protecting groups

C. Factors Governing Selectivity in Removal of Protecting Groups... 

Factors governing selectivity in removal of protecting groups / 382 Stability / 385... 

Me3SiI, CH3CN, 25-50°, 100% yield. Selective removal of protective groups is possible with this reagent since a carbamate, =NCOOCMe3, is cleaved in 6 min at 25° an aryl benzyl ether is cleaved in 100% yield, with no formation of 3-benzyltyrosine, in 1 h at 50°, at which time a methyl ester begins to be cleaved. 

SYNTHESIS OF COMPLEX SUBSTANCES TWO EXAMPLES (AS USED IN THE SYNTHESIS OF HIMASTATIN AND PALYTOXIN) OF THE SELECTION, INTRODUCTION, AND REMOVAL OF PROTECTIVE GROUPS... 

Benzyl and triphenylmethyl ethers of carbohydrates are preferred over methyl ethers when selective removal of protecting groups is important. The relatively high nucleophilic activity of the 5-hydroxyl group in glycosides and 1,2-O-alkylidene derivatives of 4 permits its benzylation and triphenylmethylation under mild conditions. Thus, treatment of 33 (Ref. 34) and 36 (Ref. 57) with benzyl bromide and... 

THE SELECTIVE REMOVAL OF PROTECTING GROUPS IN CARBOHYDRATE CHEMISTRY... 

A. H. Haines, The selective removal of protecting groups in carbohydrate chemistry, Adv. Carbokydr. Chan. Biochem. 39 13 (1981). 

Braun, P., Waldmann, H., and Kunz, H. (1992) Selective enzymatic removal of protecting functions heptyl esters as carboxy protecting groups in glycopeptide synthesis. Synlett 1, 39 10. 

Selective Removal of Protecting Groups in Carbohydrate Chemistry. Haines. A. H. Adv. Carbohydr Chem. Biochem. 1982, 59, 13 ... 

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