Can I use a primary amine to substitute (deprotect) a tosylate at high yields?

I am trying to use tosyl chloride to allow for a easy substitution of the primary alcohol on glucose then use a BOC-diamine to substitute the tosylate to form a primary amine with a short alkyl chain. But I am having trouble finding any methods in the literature that use primary or secondary amines as the nucleophile for the substitution reaction. Most use relatively stronger nuc like sodium azide or sodium ethoxide.


Is a primary amine not a strong enough nuc? And if so what methods/reagents should I use to obtain a relatively high yield?


