135357-53-8

Upstream product

• 3014-58-2 (2R,3R)-dimethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 
• 3014-58-2 dimethyl (exo,endo)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 

Downstream Products

• 1724-08-9 (+/-)-norbornane-2endo,3exo-dicarboxylic acid 
• 14253-59-9 (2R,3R)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid 
• 135357-73-2 (2S,3S)-endo-3-(Methoxycarbonyl)norbornane-exo-2-carboxylic acid 

Relevant academic research and scientific papers

Remote Exo/Endo selectivity in selective monohydrolysis of dialkyl bicyclo[2.2.1]heptane-2,3-dicarboxylate derivatives

Figure presented High exo-facial selectivity was observed in the selective monohydrolysis of a series of near-symmetric diesters that possess an exo-ester group and an endo-ester group attached on a norbornane or norbornene skeleton. The selectivities were found to be clear-cut, although the reaction center in these reactions is one covalent bond distant from the norbornane or norbornene ring, where the difference of the environment between the exo face and endo face is therefore expected to be negligible. The effect of the co-solvent we studied earlier for the selective monohydrolysis reaction was also confirmed and contributed to improvement of the yields of the half-esters.

NOVEL HEPATITIS C VIRUS INHIBITORS

The invention provides compounds of formula (I): wherein Rings A and A' are independently 5-membered optionally substituted aromatic heterocycles; Q is C(=O)NR1R1' or formula U is C(R4)2, O, S, S(=O)2, C(R4)2C(R4)2, CH2O, OCH2, CH2S, SCH2, CH2S(=O)2, S(=O)CH2 or C=C(Ru )2; X is CH2, CHR12, CR12R12, O, S, S(=O)2 or NRx; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.

Enzymatic optical resolution of norbornanecarboxylic esters using Pig Liver Esterase

The hydrolysis of a series of norbornane-type carboxylic esters catalyzed by pig liver esterase (PLE) has been investigated.It was found that an exo-ester function (syn to the C7 methylene group) is hydrolyzed with high preference.Enantioselective hydrolysis can be accomplished when a vicinal carbonyl-containing function (ester, formyl, acetyl) is present in a trans position with respect to the exo ester.The regiospecifity of the enzymatic hydrolysis has been used for the separation of exo/endo mixtures of the cycloadducts derived from cyclopentadiene and alkene esters.The regiospecifity and enantioselectivity of the enzymatic hydrolysis of norbornane-type esters were analyzed in terms of Tamm's substrate model and also by Griengl's method.

Optical and Neutron Inelastic Scattering Study of 2,3-Dimethylnorbornanes

We have measured the infrared, Raman, and neutron vibrational spectra of the 2,3-dimethylnorbornanes with two CH3 or CD3 groups in the 2- and 3-exo or endo positions.A normal-coordinate analysis has been carried out.No coupling reflecting the strain due to the methyl group appears in the C-CH3 bending and torsional modes of the trans isomer, but appears in the cis-exo isomer (average value 23 cm-1) and in the cis-endo isomer (average value 28 cm-1.The frequencies are used for the determination of the thermodynamic contribution to the standard free energy differences.