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Always use protection? The omission of a single protecting group led to the convergent synthesis of the highly branched dodecasaccharide N-glycan that contains two neighboring tetrasubstituted mannoside groups. A serendipitous finding led to the identification of the key protecting group in oligosaccharide building blocks for the optimized synthesis of N-glycans.
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Eller et al. (2007) studied this question.
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