208253-69-4

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 218766-08-6 (R)-2-(Benzhydrylidene-amino)-3-hydroxy-propionic acid methyl ester 

Downstream Products

• 208253-70-7 (2R,3R)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-2-amino-4-pentene-1,2-diol 
• 218766-10-0 (1R,2R)-2-(Benzhydrylidene-amino)-3-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-propan-1-ol 
• 218766-12-2 (4R,5R)-4-[(tert-butyldimethylsilyloxy)methyl]-5-phenyloxazolidin-2-one 
• 218766-11-1 (1R,2R)-2-amino-3-O-(tert-butyldimethylsilyl)-1-phenylpropane-1,3-diol 
• 301523-20-6 Methanesulfonic acid (S)-4-((3aS,4S,6aR)-5-benzhydryl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl)-4-(tert-butyl-dimethyl-silanyloxy)-butyl ester 
• 301523-19-3 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-N-diphenylmethyl-1,4,6,7-tetradeoxy-1,4-imino-D-gulo-octitol 
• 301523-18-2 5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-N-diphenylmethyl-1,4,6,7,8-pentadeoxy-1,4-imino-D-gulo-oct-7-enitol 
• 301523-23-9 (2R,3S)-N-diphenylmethylene-1-O-tert-butyldimethylsilyl-3-O-trimethylacetyl-2-amino-4-pentene-1,2-diol 
• 1053729-53-5 5-benzhydryl-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole 
• 301523-17-1 2,3-O-isopropylidene-N-diphenylmethyl-1,4,6,7,8-pentadeoxy-1,4-imino-D-gulo-oct-7-enitol 
• 301523-16-0 2,3-O-isopropylidene-N-diphenylmethyl-1,4-dideoxy-1,4-imino-D-lyxitol 
• 1053268-97-5 (3aS,4S,6aR)-5-Benzhydryl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carbaldehyde 

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.