Carbohydr Res 2009 Apr 21;3446:747-52. doi: 10.1016/j.carres.2009.02.003.

Synthesis of the starfish ganglioside LLG-3 tetrasaccharide.

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The first synthesis of the ganglioside LLG-3 tetrasaccharide, which has attractive biological activities as well as a unique structure, is described. A C8-methoxy decorated sialic acid building block was initially prepared and a glycolic acid moiety was then introduced by sialylation. Amide condensation between the sialyl glycolic acid and an amino group at C5 on the sialyllactoside unit afforded the fully protected LLG-3 tetrasaccharide. Finally, the desired tetrasaccharide part of LLG-3 was obtained after careful global deprotection. [structure: see text].

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