209003-96-3

Upstream product

• 211861-26-6 (3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile 
• 209003-90-7 (2R,4R,1'R)-2-(1'-benzyloxy-4'-oxobutyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 209003-89-4 (2R,4R,1'S)-2-(1'-benzyloxy-pent-4'-enyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 209003-88-3 (2R,4R,1'S)-2-(1'-hydroxy-pent-4'-enyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 211861-27-7 (2R,4R,1'R)-2-(1'-benzyloxy-4'-hydroxyhexadecyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 209003-91-8 (2R,4R,1'R)-2-(1'-benzyloxy-4'-oxohexadecyl)-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 211861-28-8 (2S,3R,6S,1'R)-2-(3-benzyloxy-6-dodecyl-2-vinylpiperidine-1-yl)-2-phenylethanol 
• 209003-93-0 (3R,5S,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine 
• 209003-87-2 (2R,4R)-2'-pent-4'-enoyl-4-phenyloxazolidine-3-carboxylic acid tert-butyl ester 
• 209003-92-9 (3R,8R,8aR)-8-Benzyloxy-5-dodecyl-3-phenyl-hexahydro-oxazolo[3,2-a]pyridine-5-carbonitrile 

Downstream Products

• 209003-98-5 (2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-vinylpiperidine 
• 209003-97-4 (2S,3R,6S)-3-benzyloxy-N-benzyloxycarbonyl-6-dodecyl-2-hydroxymethylpiperidine 

Relevant academic research and scientific papers

Selective N-dealkylation of tertiary amines derived from phenylglycinol or ephedrine family

Tertiary mines bearing an hydroxyethyl group derived from phenylglycinol, norephedrine or norpseudoephedrine can be selectively dealkylated using a two-step sequence involving treatment with thionyl chloride in THF, followed by reaction with an excess of potassium cyanide in THF:DMSO. These conditions are compatible with the presence of an insaturation or a benzyl ether in the substrate.

A new access to enantiopure β-hydroxylated piperidines from N-Boc-2- acyloxazolidines. Application to the synthesis of (-)-desoxoprosopinine and (+)-pseudoconhydrine

The synthesis of (-)-desoxoprosopinine and (+)-pseudoconhydrine were achieved from a common oxazolidine precursor. The three stereocenters present in (-)-desoxoprosopinine as well as the two stereocenters of (+)- pseudoconhydrine were created in highly stereoselective ways. The stereoselectivity observed during the reduction of the ketone moiety in the starting oxazolidine was dependent on the occurrence of a chelated intermediate. The others stereocenters arose from stereoselective reductions or alkylations of intermediate iminium ions.

Total synthesis of (-)-desoxoprosopinine via the diastereoselective reduction of homochiral2-acyl-N-Boc-oxazolidines

(-)-Desoxoprosopinine was synthesised from (R)-phenylglycinol as the chiral source. The three distinct steps used for the construction of the three stereogenic centers of the target were all highly diastereoselective. These steps include a reduction of a homochiral N-Boc-2-acyl oxazolidine and the stereoselectivity of this reaction can be explained by a non chelated model. An original N-debenzylation of the phenyl glycinol appendage was devised in this synthesis.