148903-85-9

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 102308-32-7 (4S)-4-formyl-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 
• 67-64-1 acetone 
• 100-58-3 phenylmagnesium bromide 
• 116467-54-0 (S)-tert-butyl 4-((S)-hydroxy(phenyl)methyl)-2,2-dimethyloxazolidine-3-carboxylate 

Downstream Products

• 528523-59-3 tert-butyl (4S,5S)-4-[2-(diethoxyphosphoryl)-2,2-difluoroethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate 
• 528523-58-2 tert-butyl (4S,5S)-4-[(1R)-2-(diethoxyphosphoryl)-2,2-difluoro-1-hydroxyethyl]-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate 
• 528523-61-7 (3S,4S)-1,1-difluoro-4-hydroxy-3-(palmitoylamino)-4-phenylbutylphosphonic acid 
• 528523-60-6 diethyl (3S,4S)-1,1-difluoro-4-hydroxy-3-(palmitoylamino)-4-phenylbutylphosphonate 

Relevant academic research and scientific papers

Asymmetric Morita–Baylis–Hillman Reaction: Catalyst Development and Mechanistic Insights Based on Mass Spectrometric Back-Reaction Screening

An efficient protocol for the evaluation of catalysts for the asymmetric Morita–Baylis–Hillman (MBH) reaction was developed. By mass spectrometric back-reaction screening of quasi-enantiomeric MBH products, an efficient bifunctional phosphine catalyst was identified that outperforms literature-known catalysts in the MBH reaction of methyl acrylate with aldehydes. The close match between the selectivities measured for the forward and back reaction and kinetic measurements provided strong evidence that the aldol step and not the subsequent proton transfer is rate- and enantioselectivity-determining.

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.

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.

Application of (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol in the formal total synthesis of carbapenems, novel 4-cyano-β-lactams and β-hydroxy aspartates

The imines derived from (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol furnished cis-β-lactams stereoselectively on the Staudinger reaction. These homochiral cis-β-lactams were converted in to cis-β-lactams possessing aminol side chain at C-4. These aminols

Synthesis of optically pure 4-cyano and 4-formyl cis-β-lactams via enantiospecific Staudinger reaction

Imines 1 and 2 derived from (+)-(1S,2S)-2-amino-1-phenylpropan-1,3-diol on cycloaddition reaction using acid chlorides (or equivalent) 3-6 in the presence of triethylamine furnished stereoselectively cis-β-lactams 7a-f in good yields. The aminols 8b,c on treatment with lead tetraacetate under different reaction conditions gave 4-cyano (9b,c) and 4-formyl (10b,c) β-lactams in high yields.