266338-67-4

Upstream product

• 4835-90-9 3-Hydroxy-2,2-dimethylpropanoic acid 
• 114234-21-8 2-benzyl-3-(dimethylamino)-2-methyl-2H-azirine 

Downstream Products

• 266338-90-3 1-{1-[1-({2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]-1-oxopropyl}amino)cyclopentanecarboxamido]cyclopentanecarboxamido}-N,N-dimethylcyclopentanecarboxamide 
• 266338-82-3 1-[1-({2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]-1-oxopropyl}amino)cyclopentanecarboxamido]-N,N-dimethylcyclopentanecarboxamide 
• 266338-86-7 1-[1-({2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]-1-oxopropyl}amino)cyclopentanecarboxamido]cyclopentanecarboxilic acid 
• 266338-89-0 2-[(2-{[2-({2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]-1-oxopropyl}amino)-2-methyl-1-oxopropyl]amino}-2-methyl-1-oxopropyl)amino]-2,N,N-trimethylpropanamide 
• 266338-81-2 2-{[2-({2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]-1-oxopropyl}amino)-2-methyl-1-oxopropyl]amino}-2,N-dimethyl-N-phenylpropanamide 
• 266338-85-6 2-{[2-({2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]-1-oxopropyl}amino)-2-methyl-1-oxopropyl]amino}-2-methylpropanoic acid 
• 266338-74-3 1-({2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]-1-oxopropyl}amino)-N,N-dimethylcyclopentanecarboxamide 
• 266338-78-7 1-({2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]-1-oxopropyl}amino)cyclopentanecarboxilic acid 
• 266338-73-2 2-({2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]-1-oxopropyl}amino)-2,N-dimethyl-N-phenylpropanamide 
• 266338-77-6 2-({2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]-1-oxopropyl}amino)-2-methylpropanoic acid 
• 266338-70-9 2-benzyl-2-[(3-hydroxy-2,2-dimethyl-1-oxopropyl)amino]propanoic acid 

Relevant academic research and scientific papers

14-Membered cyclodepsipeptides with alternating β-hydroxy and α-amino acids by cyclodimerization

The cyclodimerization (twinning) of β-hydroxy acid amides of type 1 under 'direct amide cyclization' (DAC) conditions is described. Although other coupling methods also gave moderate results, best yields were obtained via DAC, reaching 88% for the cyclodi

Synthesis of 16-membered cyclic depsipeptides via direct amide cyclization

The 2,2-disubstituted 2H-azirin-3-amines 5 (3-amino-2H-azirines) were used as synthons for α,α-disubstituted α-amino acids in the preparation of 16-membered cyclic depsipeptides 13. The linear precursors containing four α,α-disubstituted α-amino acids, the pentapeptides 12, were synthesized from β-hydroxy acids 4 via the 'azirine/oxazolone method' (Scheme 2). The 16-membered cyclic depsipeptides 13 were prepared via 'direct amide cyclization' in good-to-excellent yields (Schemes 3 and 4). In addition to the desired cyclic monomer 13, which was obtained as the main product, the cyclodimer 14 could also be isolated. The cyclization conditions were investigated and found to be optimum with HCl in toluene at 100°. The structure and conformation of the cyclic depsipeptide 13b was established by X-ray crystallography.