383418-15-3

Upstream product

• 383418-06-2 3-amino-4-(tert-butyl-dimethyl-silanyloxy)-thiobutyric acid S-ethyl ester 
• 383418-27-7 4-(tert-butyl-dimethyl-silanyloxy)-3-(2-hydroxy-6-methyl-phenylamino)-thiobutyric acid S-ethyl ester 
• 102191-92-4 tert-butyldimethylsiloxyacetaldehyde 
• 383418-11-9 4-(tert-butyl-dimethyl-silanyloxy)-3-dodecanoylamino-thiobutyric acid S-ethyl ester 
• 383418-13-1 dodecanoic acid [1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-3-phenyl-propyl]-amide 

Downstream Products

• 384835-42-1 (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylprop-1-yl)dodecanamide 

Relevant academic research and scientific papers

Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis

In response to Berke?'s report revising the stereochemistry of HPA-12, an important ceramide-trafficking inhibitor that was discovered and synthesized and its stereochemistry determined in 2001, the synthesis and the stereochemistry were reinvestigated. A large-scale synthetic method for HPA-12 based on a Zn-catalyzed asymmetric Mannich-type reaction in water was developed. Single crystals of HPA-12 for X-ray crystallographic analysis were obtained from ethyl propionate/n-hexane, and the stereochemistry was definitely determined to be 1R,3S, consistent with Berke?'s revised structure.

Catalytic enantioselective synthesis of a novel inhibitor of ceramide trafficking, (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)-dodecanamide (HPA-12)

A novel inhibitor of ceramide trafficking, (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12), has been synthesized using a chiral zirconium-catalyzed asymmetric Mannich-type reaction as a key-step.