39508-36-6

Upstream product

• 15190-13-3 (4-methoxy-phenyl)-morpholin-4-yl-acetonitrile 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 19486-71-6 p-methoxybenzaldehyde-d1 
• 1426955-81-8 (R)-(-)-4-methoxybenzyl-α-d chloride 
• 118070-14-7 <(1R)-<1-²H>-4-methoxybenzyl> (2S)-2-acetoxy-2-phenylethanoate 
• 118063-61-9 N-phthaloyl (1S)-<1-²H>-4-methoxybenzylamine 
• 118063-60-8 (1S)-<1-²H> N-t-butyloxycarbonyl 4-methoxybenzylamine 
• 124176-47-2 (1R)-<1-²H>-4-methoxybenzylalcohol 
• 70719-19-6 (S)-[α-(2)H]-p-methoxybenzyl alcohol 

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

Improved synthesis of (R)-glycine-d-15N

Previously, we have synthesized the title glycine to permit assignment of the prochiral α-protons of glycine residues in the NMR study of the protein FKBP. A key, and low yielding step in this synthesis occurs in the ruthenium tetraoxide mediated degradation of N-t-Boc-p-methoxybenzyl amine to N-t-Boc-glycine. Efforts to improve this key step by exploring different substrates and N-protecting groups were successful to render this synthesis amenable for the large scale production of (R)-glycine-d-15N.

A Practical Large Scale Chemical Synthesis of Chiral Glycines

(R)- and (S)-2H>glycine of high chiral purity were synthesized in large quantities in ca.40percent overall yield from readily available starting materials via a totally chemical procedure.Reduction of either 2H>-furfural or 2H>-4-methoxybenzaldehyde with either (+) or (-)-B-isopinocampheyl-9-borabicyclononane gave chiral arylmethyl alcohols which were converted into their respective phthaloyl amino derivatives of the opposite configuration at the methylene carbon via the Mitsunobu reaction.The aromatic groups were oxidatively unmasked to give their corresponding glycine derivatives by either ozone or ruthenium tetraoxide oxidation.