title: Concise synthesis of α-galactosyl ceramide from D-galactosyl iodide and D-lyxose.
abstract: 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.
authors: Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan.
authors: Yu-Fen
authors: YF
authors: Yen
authors: Suvarn S
authors: SS
authors: Kulkarni
authors: Chun-Wei
authors: CW
authors: Chang
authors: Shun-Yuan
authors: SY
authors: Luo
mesh_terms: D005699:Galactosylceramides / Q000138:chemical synthesis* / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D010429:Pentoses / Q000737:chemistry*
chemical_list: D005699:Galactosylceramides; D007454:Iodides; D010429:Pentoses; C493154:alpha-galactosylceramide; C043333:lyxose; C103873:KRN 7000