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Concise synthesis of α-galactosyl ceramide from d-galactosyl iodide and d-lyxose

By Yu-Fen Yen, Suvarn S. Kulkarni, Chun-Wei Chang and Shun-Yuan Luo


α-Galactosyl ceramide is synthesized from d-lyxose in 32% overall yield in five steps. The short and efficient protocol involves a one-pot protection and glycosidation of d-lyxose with d-galactosyl iodide as a key step. The α-linked disaccharide obtained was subsequently transformed into α-galactosyl ceramide in four steps involving Z-selective Wittig olefination at C-1, stereo-inversion at C-4 using azide, one-pot reduction of azide and amidation, and global deprotection

Topics: α-Galactosyl ceramide, KRN7000, Glycosyl iodide, One-pot protection-glycosylation, Wittig reaction
Year: 2014
DOI identifier: 10.1016/j.carres.2012.11.008
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