320343-41-7

Upstream product

• 81028-12-8 (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 78469-77-9 (4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 320343-43-9 (2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol 
• 145401-48-5 sphingofungin F 
• 320343-42-8 (2E,4S,5S)-1-hydroxy-2-methyl-4,5-O-isopropylidene-6-(benzyloxy)hex-2-ene-4,5-diol 

Relevant academic research and scientific papers

An efficient and convenient approach to the total synthesis of sphingofungin

As a new member of the sphingofungin family, sphingofungin F exhibits interesting physiological activities with a structural unit of an α-substituted alanine. Described herein is an efficient and convenient stereoselective synthesis of sphingofungin F from L-(+)-tartaric acid, which utilizes Sharpless asymmetric epoxidation of allylic alcohol and Lewis acid-catalyzed intramolecular epoxideopening reaction with an N-nucleophile, to introduce the other two desired stereogenic centers. Side chain functionality was incorporated into the chiral segment using a Wittig reaction.