218766-15-5

Upstream product

• 110-91-8 morpholine 
• 218766-13-3 (4R,5R)-(+)-4-(4'-p-toluenesulfonyloxymethyl)-5-phenyloxazolidin-2-one 
• 1236068-31-7 (2R,3R)-4-(1-tert-butoxycarbonyl-3-phenylaziridine-2-ylmethyl)morpholine 
• 1236068-33-9 (1S,2R)-1-phenyl-2-tert-butoxycarbonylamino-3-(N-morpholino)-1-bromopropane 
• 1353580-54-7 (2'S,3'S)-4-(3'-phenyloxiran-2'-ylmethyl)morpholine 
• 1353580-55-8 C₁₃H₁₈N₂O 
• 104-54-1 3-Phenylpropenol 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 218766-10-0 (1R,2R)-2-(Benzhydrylidene-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-propan-1-ol 
• 218766-11-1 (1R,2R)-2-amino-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol 

Downstream Products

• 109760-77-2 D-threo-1-ethylendioxyphenyl-2-decanoylamino-3-pyrrolidinopropanol 
• 218766-23-5 (1R,2R)-2-amino-3-(N-morpholino)-1-phenylpropan-1-ol 

Relevant academic research and scientific papers

New highly efficient stereoselective synthesis of d-threo-PDMP

Starting from a suitably functionalized aziridine, a highly efficient stereoselective synthesis of (1R,2R)-phenyl-2-decanoyl-amino-3-morpholinopropan- 1-ol (d-threo-PDMP) is described. The approach, based on the ring expansion of the aziridine ring to oxa

MgBr2-mediated opening of 2,3-three membered heterocyclic amines

(Chemical Equation Presented) Regio- and stereo-controlled opening of 2,3-epoxy amines and 2,3-aziridine amines by the commercially available MgBr2 is described. As reported, this new method could represent a general and useful approach for the preparation of promising intermediates. Moreover, in particular cases, the reaction evolves toward an interesting oxazolidin-2-one structure.

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.