189246-47-7

Upstream product

• 189246-46-6 (3R,6R)-2,5-Diethoxy-3,6-dimethyl-3,6-dihydropyrazin 
• 181211-21-2 (E)-(2R,3S)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-octadec-4-enal 
• 181495-46-5 (4R,5R)-5-benzyloxy-4-(2-trimethylsilylethynyl)-2,2-dimethyl-1,3-dioxane 
• 181211-20-1 ((E)-(S)-1-{(S)-1-Benzyloxy-2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-hexadec-2-enyloxy)-tert-butyl-dimethyl-silane 
• 181210-41-3 (E)-(2S,3S)-2-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-octadec-4-en-1-ol 
• 181211-18-7 (4S,5S)-5-Benzyloxy-2,2-dimethyl-4-pentadec-1-ynyl-[1,3]dioxane 
• 181211-19-8 (2S,3S)-2-Benzyloxy-octadec-4-yne-1,3-diol 
• 181434-86-6 (4S,5S)-5-benzyloxy-4-ethynyl-2,2-dimethyl-1,3-dioxane 
• 765-09-3 1-bromotridecane 

Downstream Products

• 189246-49-9 (E)-(2S,3R,4R,5S)-2-Amino-4-benzyloxy-3,5-dihydroxy-2-methyl-icos-6-enoic acid 
• 189246-48-8 (E)-(1R,2R,3S)-2-Benzyloxy-1-((2S,5R)-3,6-diethoxy-2,5-dimethyl-2,5-dihydro-pyrazin-2-yl)-octadec-4-ene-1,3-diol 

Relevant academic research and scientific papers

Catalytic asymmetric syntheses of antifungal sphingofungins and their biological activity as potent inhibitors of serine palmitoyltransferase (SPT)

Unambiguous synthetic routes to sphingofungins B and F and to their stereoisomers have been developed based on the tin(II)-catalyzed asymmetric aldol reaction (Chiral Lewis Acid-Controlled Synthesis (CLAC Synthesis)). Efficient enantioselective synthesis using a catalytic amount of a chiral source as well as the effectiveness of this strategy for the synthesis of the sphingofungin family have been successfully demonstrated. Using the stereoisomers of sphingofungin B synthesized, the relevance of its stereochemistry to its SPT inhibitory activity has been revealed.

The Asymmetric Synthesis of Sphingofungin F and the Determination of Its Stereochemistry

The asymmetric synthesis of sphingofungin F has been achieved and its stereochemistry has been determined. Its structure, including the absolute configuration of the chiral centers, was found to be similar to that of sphingofungin B or myriocin. The synth