4181-91-3

Upstream product

• 3481-15-0 benzyl alcohol-d1 
• 130583-32-3 C₈H₆⁽²⁾HClN₂O 
• 3481-15-0 (S)-[α-D]-benzyl alcohol 
• 26593-35-1 α-phenyl-4-morpholineacetonitrile-α-d 
• 3592-47-0 Benzaldehyde-d 
• 15190-10-0 morpholin-4-yl-phenyl-acetonitrile 
• 100-52-7 benzaldehyde 
• 4181-90-2 (R)-(α-2H)benzyl alcohol 
• 130583-31-2 α-deuteriobenzylisourea tosylate 

Downstream Products

• 84369-11-9 (S)-(-)-(.alfa.-deuteriobenzyl)tributyltin 
• 1217271-34-5 (R,S)-[palladium(II)(chloride)(monodeuteriobenzyl)(2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl)] 

Relevant academic research and scientific papers

Chirally deuterated benzyl chlorides from benzyl alcohols via hexachloroacetone/polymer-supported triphenylphosphine: Synthesis of protected (2S, 3S)-[3-2H, 15N]-tyrosine

Chirally deuterated benzyl chlorides were prepared using novel, general hexachloroacetone/polymer-supported triphenylphosphine treatment of chirally deuterated benzyl alcohols. Doubly labeled protected tyrosine was obtained in 62% yield with 86% de at the α-carbon and 82% de at the β-carbon. Key in the synthesis was the alkylation of 15N-labeled (-)-8-phenylmenthylhippurate with R-(-)-4-triisopropylsilyloxybenzyl-α-d chloride. Chirally deuterated benzyl chlorides were prepared in high yield with inversion from benzyl alcohols using solid-phase methods. One of the benzyl chlorides obtained was used in the synthesis of protected tyrosine labeled with 15N and chirally deuterated on the β-position. Copyright

Stereoselective route to 15N-labeled-β-deuterated amino acids: Synthesis of (2S,3R)-[3-2H,15N]-phenylalanine

(2S,3R)-[3-2H,15N]-Phenylalanine hydrochloride was synthesized utilizing 15N-labeled 8-phenylmenthylhippurate as a chiral glycine equivalent. The key step in the synthesis was the alkylation of the glycine template with (S)-(+)-benzyl-α-d-mesylate. The doubly labeled alkylation product was obtained in 89% yield with 92% de at the α-carbon and 74% de at the β-carbon. The nature of the electrophile employed in the alkylation step significantly affects the stereochemical outcome at the β-carbon. Hydrolysis of the alkylation product under acidic conditions followed by recrystallization from isopropanol yielded the title compound as the hydrochloride salt. Analysis of the (-)-camphanamide derivative of the final product by NMR spectroscopy and HPLC revealed a 76% de at the α-carbon and a 72% de at the β-carbon. The synthetic strategy described represents a simple yet versatile route to chirally deuterated β-methylene unit containing amino acids.

The stereochemical course of fragmentation of benzyloxychlorocarbene

The fragmentation of α-deuteriobenzyloxychlorocarbene to α-deuteriobenzyl chloride in acetonitrile occurs with at least 60% net retention of stereochemistry.