186525-69-9

Upstream product

• 172214-80-1 (1S,5S,6S,7S,1'S)-(+)-6-acetyloxy-2,3-diaza-7-(1',2'-epoxyethyl-1'-methoxycarbonyl)-1-methoxycarbonylbicyclo<3.3.0>oct-2-ene 
• 172214-83-4 (1R,3S,4S,5S,1'S)-(+)-4-acetyloxy-3-(1',2'-epoxy-ethyl-1'-methocarbonyl)-1-methoxycarbonylbicyclo<3.1.0.>hexane 
• 172214-79-8 (3S,4S,1'S)-(+)-3-acetoxy-4-(1',2'-epoxyethyl-1'-methoxycarbonyl)cyclopent-1-ene-1-carboxylic acid methyl ester 
• 172214-78-7 (3S,4S,1'S)-(+)-4-(1',2'-epoxyethyl-1'-methoxycarbonyl)-3-hydroxycyclopent-1-ene-1-carboxylic acid methyl ester 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 172214-85-6 (1R,3S,4S,5S,1'S)-(+)-4-acetyloxy-3-(1'-hydroxy-1'-methoxycarbonyl-1'-<(R)-α-methylbenzylaminomethyl>methyl)-1-methoxycarbonylbicyclo<3.1.0>hexane 

Relevant academic research and scientific papers

Enantioselective synthesis of novel homochiral α-substituted (S)-isoserine derivatives. Incorporation of this amino acid in a highly conformationally constrained dipeptide surrogate

Optically pure isoserine derivatives with a chiral polyfunctional bicyclo[3.1.0]hexyl substituent at the α-carboxyl position were synthesized from a common cyclopentene precursor bearing an α-epoxy ester function in a side-chain. Cyclopropanation of the double bond and nucleophilic oxirane-ring opening by using a homochiral amine were the key steps. One of the synthesized derivatives was condensed with Cbz-cyclo-Asp-OMe affording a highly conformationally constrained dipeptide surrogate.