437768-95-1

Upstream product

• 938055-35-7 (S)-N-(p-methoxybenzyl)-N-(bromoacetyl)valine methyl ester 
• 1456900-67-6 (S)-methyl 2-(2-chloro-N-(4-methoxybenzyl)acetamido)-3-methylbutanoate 
• 6306-52-1 L-valine methylester hydrochloride 
• 72-18-4 L-valine 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 

Downstream Products

• 852994-84-4 (3S)-N-1-(tert-butoxycarbonyl)-N-4-(4-methoxybenzyl)-3-isopropyl-piperazine-2,5-dione 
• 938055-36-8 (S)-N⁽¹⁾-methyl-N⁽⁴⁾-(p-methoxybenzyl)-3-isopropylpiperazine-2,5-dione 
• 72-18-4 L-valine 
• 2462-34-2 L-valine benzyl ester hydrochloride 
• 1456900-73-4 (S)-5-ethoxy-6-isopropyl-1-(4-methoxybenzyl)-1,6-dihydropyrazin-2(3H)-one 
• 1456900-63-2 (S)-2-((R)-2-amino-3-(4-oxocyclohexyl)propanamido)-3-methylbutanoic acid 
• 1456900-77-8 (3R,6S)-5-ethoxy-6-isopropyl-1-(4-methoxybenzyl)-3-((4-oxocyclohexyl)methyl)-1,6-dihydropyrazin-2(3H)-one 
• 1464802-73-0 C₃₀H₅₀N₂O₄Si 

Relevant academic research and scientific papers

The synthesis and biological testing of bacilysin analogues

A series of compounds based on the structure of bacilysin were synthesised and tested for antibacterial activity. The key steps in the syntheses are the coupling of an iodide to a diketopiperazine (DKP) and mono-lactim ether scaffold, respectively. The diastereoselectivity of the coupling reactions was dependant on the scaffold, with selectivity for DKP of about 4:1 and mono-lactim ether exceeding 98:2. Subsequent elaboration of the compounds to give open chain dipeptides and DKPs that mimic the structure of bacilysin but substitute the epoxy ketone for a saturated or unsaturated ketone is described. Overall yield from coupling to final product was between 5 and 21 %, with the yield of the saturated products notably higher. The open chain dipeptides demonstrated moderate antibacterial and antifungal activity.

On the origins of diastereoselectivity in the alkylation of diketopiperazine enolates

High levels of diastereoselectivity are observed for benzylation of the lithium enolates of (S)-N,N′-bis-para-methoxybenzyl-3-iso-propyl- piperazine-2,5-dione, (S)-N(1)-para-methoxybenzyl-N(4)-methyl-3-iso-propyl- piperazine-2,5-dione and (S)-N(1)-methyl-

Diastereoselective synthesis of quaternary α-amino acids from diketopiperazine templates

Sequential enolate alkylations of (S)-N(1)-methyl-5-methoxy-6-isopropyl-3, 6-dihydropyrazin-2-one and (S)-N(1)-p-methoxybenzyl-5-methoxy-6-isopropyl-3,6- dihydropyrazin-2-one proceed with excellent levels of diastereoselectivity (>90% de) affording quaternary α-amino acids in high enantiomeric excess (>98% ee) after deprotection and hydrolysis. This journal is The Royal Society of Chemistry.

1-Alkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones as glycine templates. Synthesis of fiscalin B

An excess of base allows the regio- and diastereoselective alkylation at C(4) of the glycine templates 1-methyl(isopropyl)-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones 9a and 9b without the need for N(2)-protecting groups. While the alkylation of