Stereoselective synthesis of the trisaccharide moiety of ganglioside HLG-2

The Journal of Organic Chemistry
Fei-Fei XuXin-Shan Ye

Abstract

The glycan portion of ganglioside HLG-2, which was identified in the extracts of the sea cucumber Holothuria leucospilota , was synthesized in a highly efficient and stereoselective manner. The unusual sequence of the trisaccharide moiety, α-N-glycolylsialyl-(2,4)-α-N-acetylsialyl-(2,6)-glucoside, was assembled by stereoselective coupling of a 5-N,4-O-carbonyl-protected sialyl phosphate donor, a N-2,2,2-trichloroethoxycarbonyl (Troc)-protected sialyl acceptor, and a (trimethylsilyl)ethyl-β-glucosyl acceptor in high yield. The synthesis featured the high-yielding construction of two α-sialyl linkages.

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Citations

Nov 6, 2015·Organic Letters·Run-Ze MaoXin-Shan Ye
Aug 24, 2018·Marine Drugs·Iván Cheng-Sánchez, Francisco Sarabia

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