183181-99-9

Upstream product

• 98-88-4 benzoyl chloride 
• 638-45-9 1-Iodohexane 
• 139119-52-1 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one 
• 143870-65-9 1-benzoyl-2(S)-tert-butyl-6(S)-carboxy-perhydropyrimidin-4-one 
• 143870-67-1 1-benzoyl-2(S)-tert-butyl-3-methyl-2,3-dihydro-4(1H)-pyrimidin-4-one 
• 143870-66-0 1-benzoyl-2(S)-tert-butyl-2,3-dihydro-4(1H)-pyrimidin-4-one 

Downstream Products

• 183182-03-8 (2S,5S)-1-Benzoyl-2-tert-butyl-5-hexyl-3-methyl-tetrahydro-pyrimidin-4-one 
• 255871-57-9 (2S,5R)-1-benzoyl-2-tert-butyl-3-methyl-5-benzyl-5-n-hexylperhydropyrimidin-4-one 

Relevant academic research and scientific papers

Enantioselective synthesis of β-amino acids. Part 10: Preparation of novel α,α- and β,β-disubstituted β-amino acids from (S)-asparagine

Perhydropyrimidinone (S)-1 is alkylated with very high diastereoselectivity to give trans products (2S,5R)-3, (2S,5R)-4 and (2S,5R)- 5. Dialkylation of (S)-1 also proceeds with complete stereoselectivity to afford adducts (2S,5R)-6, (2S,5S)-6, (2S,5R)-7 a

Enantioselective synthesis of β-amino acids. 7. Preparation of enantiopure α-substituted β-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one

Inexpensive natural α-amino acid L-asparagine was efficiently converted to either (R)- or (S)-α-alkylated β-amino acids in enantiomerically pure state. The key intermediate in this protocol is the enantiopure N,N-acetal pyrimidinone (S)-1, a masked chiral derivative of β-alanine.