Concise synthesis of a-galactosyl ceramide from D-galactosyl iodide and D-lyxose.

Carbohydrate research

PubMedID: 23333444

Yen YF, Kulkarni SS, Chang CW, Luo SY. Concise synthesis of a-galactosyl ceramide from D-galactosyl iodide and D-lyxose. Carbohydr Res. 2013;36835-9.
a-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 a-linked disaccharide obtained was subsequently transformed into a-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.