853013-12-4Relevant articles and documents
An efficient synthesis of D-ribo- and L-lyxo-phytosphingosine from D-tartaric acid
Lu, Xuequan,Bittman, Robert
, p. 3165 - 3168 (2007/10/03)
The preparations of D-ribo- and L-lyxo-phytosphingosines (1, 2) are described. Chelation-controlled addition of tetradecylmagnesium bromide to pentylidene-protected D-threitol aldehyde 6 afforded the key intermediate tetrol 7, providing the desired L-lyxo stereochemistry of phytosphingosine. Inversion at C4 of intermediate 7 provided the D-ribo stereochemistry.