350503-44-5

Upstream product

• 100-58-3 phenylmagnesium bromide 
• 102308-32-7 (4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 116467-53-9 (S)-4-((R)-Hydroxy-phenyl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 528523-45-7 tert-butyl (1S,2S)-1-({[tert-butyl(diphenyl)silyl]oxy}methyl)-2-hydroxy-2-phenylethylcarbamate 
• 167082-56-6 tert-butyl [(1S,2S)-1,3-dihydroxy-1-phenylpropan-2-yl]carbamate 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 183075-33-4 tert-butyl (1,3-dihydroxy-1-phenylpropan-2-yl)carbamate 

Downstream Products

• 350503-45-6 tert-butyl (4S,5R)-4-hydroxymethyl-2,2-dimethyl-5-phenyl-1,3-oxazolidin-3-carboxylate 
• 528523-49-1 (4R,5R)-4-Formyl-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 528523-52-6 tert-butyl (4S,5R)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate 
• 528523-50-4 (4S,5R)-4-[(R)-2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 528523-56-0 diethyl (3S,4R)-1,1-difluoro-4-hydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate 
• 528523-54-8 diethyl (2R,3S,4R)-1,1-difluoro-2,4-dihydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate 
• 207278-84-0 (4S,5R)-2,2-Dimethyl-4-morpholin-4-ylmethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 207278-83-9 (4S,5R)-4-Methanesulfonyloxymethyl-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 350503-47-8 ((3R,4R)-1,1-Difluoro-2,4-dihydroxy-3-octadecanoylamino-4-phenyl-butyl)-phosphonic acid diethyl ester 
• 350503-46-7 (4S,5R)-4-[2-(Diethoxy-phosphoryl)-2,2-difluoro-1-hydroxy-ethyl]-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 207278-82-8 (4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Synthesis of non-competitive inhibitors of sphingomyelinases with significant activity

A series of short-chain analogues of N-palmitoylsphingosine-1-phosphate, modified by replacement of the phosphate and the long alkenyl side chain with hydrolytically stable difluoromethylene phosphonate and phenyl, respectively, were prepared to study the structure-activity relationship for inhibition of sphingomyelinase. The study revealed that inhibition is highly dependent upon the stereochemistry of the asymmetric centers of the acylamino moiety, and resulted in identification of a non-competitive inhibitor with the same level of inhibitory activity of schyphostatin, the most potent of the few known small molecular inhibitors of sphingomyelinase.

Synthesis and evaluation of a difluoromethylene analogue of sphingomyelin as an inhibitor of sphingomyelinase

A sphingomyelin analogue 2, in which the long alkenyl chain and the phosphodiester moiety of sphingomyelin were replaced by a phenyl and an isosteric difluoromethylenephosphonic acid, was prepared to evaluate its inhibitory potency to sphingomyelinase. The analogue non-competitively inhibited the neutral sphingomyelinase in bovine brain microsomes with an IC50 of 400 μM. The compound had the ability to suppress tumor necrosis factor α-induced apoptosis of PC-12 neurons at a low concentration of 0.1 μM.

Practical synthesis of threo-(1S, 2S)- and erythro-(1R, 2S)-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) from L-serine

Both L-threo and D-erytho-1-phenyl-2-palmitoylamino-3-morpholino-1-propanol (PPMP) were synthesized stereoselectively from L-serine.