367259-01-6

Upstream product

• 763-32-6 2-methyl-1-buten-4-ol 
• 100-39-0 benzyl bromide 
• 58558-53-5 (((3-methylbut-3-en-1-yl)oxy)methyl)benzene 
• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 

Downstream Products

• 426825-46-9 (2S,4R)-1-((S)-2-Benzyloxycarbonylamino-2-cyclohexyl-acetyl)-4-(3-benzyloxy-1,1-dimethyl-propoxy)-pyrrolidine-2-carboxylic acid methyl ester 
• 426825-47-0 (2S,4R)-1-{(S)-2-Cyclohexyl-2-[2-(3-hydroxy-phenyl)-acetylamino]-acetyl}-4-(3-hydroxy-1,1-dimethyl-propoxy)-pyrrolidine-2-carboxylic acid methyl ester 
• 367261-09-4 12-cyclohexyl-5,5-dimethyl-11,14-dioxo-2,6-dioxa-10,13-diazatricyclo[14.3.1.1^7,10]henicosa-1⁽¹⁹⁾,16⁽²⁰⁾,17-triene-9-carboxylic acid methyl ester 
• 367259-79-8 (2S,4R)-1-((S)-2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-4-(3-hydroxy-1,1-dimethyl-propoxy)-pyrrolidine-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Syntheses of novel 4-tert-alkyl ether proline-based 16- and 17-membered macrocyclic compounds

Starting from N-Cbz-4-hydroxyproline methyl ester 1, a boron trifluoride-diethyl etherate-catalyzed reaction provided 4-tert-alkyl ether proline 4. Two deprotections and amide bond formations furnished the phenol alcohol 2. The macrocyclization of 2 was accomplished through a Mitsunobu reaction using triphenylphosphine and 1,1′-(azodicarbonyl)dipiperidine (ADDP), to afford novel 16- and 17-membered proline-based macrocyclic compounds of type 3.