218766-13-3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 127870-56-8 (4R,5R)-4-Hydroxymethyl-5-phenyl-oxazolidin-2-one 
• 218766-10-0 (1R,2R)-2-(Benzhydrylidene-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-propan-1-ol 

Downstream Products

• 218766-22-4 (4R,5R)-5-Phenyl-4-pyrrolidin-1-ylmethyl-oxazolidin-2-one 
• 109760-77-2 D-threo-1-ethylendioxyphenyl-2-decanoylamino-3-pyrrolidinopropanol 
• 193545-88-9 (1R,2R)-2-Amino-3-pyrrolidino-1-phenyl-1-propanol 
• 218766-25-7 (1R,2R)-2-Amino-1-phenyl-3-piperidin-1-yl-propan-1-ol 
• 218766-24-6 (1R,2R)-2-Amino-1-phenyl-3-thiomorpholin-4-yl-propan-1-ol 
• 218766-23-5 (1R,2R)-2-amino-3-(N-morpholino)-1-phenylpropan-1-ol 
• 193545-89-0 (1R,2R)-2-decanoylamino-3-pyrrolidino-1-phenyl-1-propanol 
• 218766-16-6 (4R,5R)-5-Phenyl-4-thiomorpholin-4-ylmethyl-oxazolidin-2-one 
• 218766-15-5 (4R,5R)-4-(morpholin-4-ylmethyl)-5-phenyloxazolidin-2-one 
• 218766-21-3 (4R,5R)-5-Phenyl-4-piperidin-1-ylmethyl-oxazolidin-2-one 

Relevant academic research and scientific papers

Glycosyltransferase inhibitors: Synthesis of D-threo-PDMP, L-threo- PDMP, and other brain glucosylceramide synthase inhibitors from D- or L- serine

The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2- decanoylamino-3-N-morpholino-1-propanol (L-threo-PDMP) (1a) from L-serine, and the enantiomer (LR,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (1b) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the β-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure 1b in high yield after six steps. Three other D- threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D- threo-PDPP (1e). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.