A textbook of organic chemistry by Chamberlain JS

By Chamberlain JS

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45 Disaccharide 66 was extended in standard fashion to trisaccharide 67 and fully protected to give 68. This latter compound was treated with anthracenesulfonamide and I(sym-coll)2ClO4 to form the intermediate 69. Reaction of the iodosulfonamide 69 with tetra-n-butylammonium azide followed by acetylation provided the anomeric azide 70. The anthracenesulfonamide linkage was cleaved under mild, solid support compatible conditions such as thiophenol or 1,3-propanedithiol and Hünig’s base. 3 Complex-type biantennary structure.

22 Synthesis of N-linked glycopeptides on a solid support. 23 Solid-phase synthesis of glycopeptides. give glycopeptide 86. Retrieval from the solid support afforded trisaccharide– octapeptide 87 in 18% overall yield from 10. The methodology described above has proved to be effective for other glycosylation sequences. 23 shows conversion of a variety of disaccharides to their respective glycopeptides. For example, lactal derivative 31 was transformed into a lactosamine-linked glycopeptide where C6 of the glucosamine residue is protected as its benzyl ether, in 24% overall yield.

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