Work from the Wong Laboratory

We have demonstrated an orthogonal protection/deprotection strategy for preparing a carbohydrate core that could be iteratively deprotected and glycosylated to form 

We use the term programmable to describe the rational (and ideally, computer-aided and automated) approach to polysaccharide synthesis.20 To reduce the synthesis of complex carbohydrates to routine, we envision a four-step protocol (1) the sequence of interest is keyed into a computer, (2) the computer selects appropriate reagent combinations, (3) a laboratory worker (human or robotic) prepares the reagent 

1 Strategy Our strategy for one-pot methods rested on using common anomeric groups, and a common activator. We chose p-methylphenyl thioglycosides (STol) as our donor species for three reasons  

Thioglycosides can be activated by a wealth of strategies,3,4 although our investigations center on the use of electrophilic iodine (7V-iodosuccinimide). 

The thiotoluoyl group offers a convenient spectroscopic handle. 

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