853013-10-2

Upstream product

• 753020-02-9 (2R,3S)-2-O-benzyl-3,4-O-(3'-pentylidene)-2,3,4-trihydroxybutanal 
• 88303-25-7 tetradecylmagnesium bromide 
• 853013-11-3 (1R,2S)-1-Benzyloxy-1-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-hexadecan-2-ol 

Relevant academic research and scientific papers

An efficient synthesis of D-ribo- and L-lyxo-phytosphingosine from D-tartaric acid

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.