506444-80-0

Basic information

• Product Name: (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid
• Synonyms: (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid
• CAS NO: 506444-80-0
• Molecular Weight: 333.341
• Mol File: 506444-80-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid(506444-80-0)
• EPA Substance Registry System: (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-carboxylic acid(506444-80-0)

Safety Data

• Hazardous Substances Data: 506444-80-0(Hazardous Substances Data)

Upstream product

• 152839-68-4 4-(methoxycarbonyl)benzyl trans-1,3-butadiene-1-carbamate 
• 506444-78-6 (3'S,4'S,4S)-3'-(N'-p-methoxycarbonylbenzyloxycarbonylamino-1'-cyclohexene-4'-carbonyl)-[4-tert-butyl-2'-oxazolidinone] 
• 6908-41-4 4-(methoxycarbonyl)benzyl alcohol 

Downstream Products

• 5691-19-0 rac-trans-2-aminocyclohexanecarboxylic acid 
• 506444-82-2 (3S,4S)-3-(N'-p-methoxycarbonylbenzyloxycarbonylamino)-1-cyclohexene-4-N,N-dimethylcarboxamide 

Relevant articles and documents

Experimental determination of the absolute enantioselectivity of an antibody-catalyzed Diels-Alder reaction and theoretical explorations of the origins of stereoselectivity

The exo and endo Diels-Alder adducts of p-methoxycarbonylbenzyl trans-1,3-butadiene-1-carbamate and N,N-dimethylacrylamide have been synthesized, and the absolute configurations of resolved enantiomers have been determined. On the basis of this information, the absolute enantioselectivities of the Diels-Alder reaction catalyzed by antibodies 13G5 and 4D5 as well as other catalytic antibodies elicited in the same immunizations have been established. The effects of different arrangements of catalytic residues on the structure and energetics of the possible Diels-Alder transition states were modeled quantum mechanically at the B3LYP/6-311++G**//B3LYP/6-31+G** level of theory. Flexible docking of these enantiomeric transition states in the antibody active site followed by molecular dynamics on the resulting complexes provided a prediction of the transition -state binding modes and an explanation of the origin of the observed enantioselectivity of antibody 13G5.