24332-67-0

Upstream product

• 652-67-5 Isosorbide 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 93-97-0 benzoic acid anhydride 
• 876385-20-5 isosorbide-2-(butylcarbamate)-5-benzoate 
• 1072106-11-6 isosorbide-2-benzylcarbamate-5-benzoate 

Downstream Products

• 186420-28-0 Benzoic acid (3R,3aR,6S,6aS)-6-trifluoromethanesulfonyloxy-hexahydro-furo[3,2-b]furan-3-yl ester 
• 157904-95-5 1,4:3,6-dianhydro-5-O-(phenylcarbonyl)-D-fructose 
• 1072106-20-7 isosorbide-2-(3,4-dichlorophenylcarbamate)-5-benzoate 
• 876385-20-5 isosorbide-2-(butylcarbamate)-5-benzoate 
• 650577-58-5 1,4:3,6-dianhydro-2-deoxy-5-O-(phenylcarbonyl)-L-arabino-hex-1-enitol 
• 186420-50-8 Benzoic acid (3R,3aS,6R,6aR)-6-[2-amino-6-chloro-5-(4-chloro-phenylazo)-pyrimidin-4-ylamino]-hexahydro-furo[3,2-b]furan-3-yl ester 
• 186420-51-9 Benzoic acid (3R,3aS,6R,6aR)-6-(2,5-diamino-6-chloro-pyrimidin-4-ylamino)-hexahydro-furo[3,2-b]furan-3-yl ester 
• 186420-48-4 Benzoic acid (3R,3aS,6R,6aR)-6-(5-amino-6-chloro-pyrimidin-4-ylamino)-hexahydro-furo[3,2-b]furan-3-yl ester 
• 186420-40-6 Benzoic acid (3R,3aS,6R,6aR)-6-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,2-b]furan-3-yl ester 
• 186420-49-5 Benzoic acid (3R,3aS,6R,6aR)-6-(2-amino-6-chloro-pyrimidin-4-ylamino)-hexahydro-furo[3,2-b]furan-3-yl ester 
• 186420-46-2 Benzoic acid (3R,3aS,6R,6aR)-6-(2-oxo-4-thioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,2-b]furan-3-yl ester 
• 186420-42-8 Benzoic acid (3R,3aS,6R,6aR)-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-hexahydro-furo[3,2-b]furan-3-yl ester 

Relevant academic research and scientific papers

Oxidative NHC-Catalysis as Organocatalytic Platform for the Synthesis of Polyester Oligomers by Step-Growth Polymerization

The application of N-heterocyclic carbene (NHC) catalysis to the polycondensation of diols and dialdehydes under oxidative conditions is herein presented for the synthesis of polyesters using fossil-based (ethylene glycol, phthalaldehydes) and bio-based (

Practical and scalable synthesis of isosorbide derivatives containing an active amine group

The synthesis of two derivatives of isosorbide containing an amine group, 6-amino-6-deoxy-O-3-methyl-isosorbide and 6-amino-O-3-benzoyl-6-deoxy-isosorbide, has been achieved. These compounds provide scope for the introduction of additional groups via thei

3+2-Dipolar cycloaddition of dianhydrohexitol azidoderivatives with N-arylmaleimides

Abstract Dianhydrohexitol azides dipolar 3+2 cycloaddition with N-arylmaleimides has been studied with NMR (1H and 13C, COSY, NOESY and HSQC) and X-ray analysis. In spite of low asymmetrical induction in this reaction, diastereomeric

Isosorbide-2-benzyl carbamate-5-salicylate, a peripheral anionic site binding subnanomolar selective butyrylcholinesterase inhibitor

Isosorbide-2-benzyl carbamate-5-benzoate is a highly potent and selective BuChE inhibitor. Meanwhile, isosorbide-2-aspirinate-5-salicylate is a highly effective aspirin prodrug that relies on the salicylate portion to interact productively with human BuChE. By integrating the salicylate group into the carbamate design, we have produced isosorbide-2-benzyl carbamate-5-salicylate, an inhibitor of high potency (150 pM) and selectivity for human BuChE over AChE (666000) and CES2 (23000). Modeling and mutant studies indicate that it achieves its exceptional potency because of an interaction with the polar D70/Y332 cluster in the PAS of BuChE in addition to pseudosubstrate interactions with the active site.

Isosorbide-2-carbamate esters: Potent and selective butyrylcholinesterase inhibitors

In this study, we report the SAR and characterization of two groups of isosorbide-based cholinesterase inhibitors. The first was based directly on the clinically used nitrate isosorbide mononitrate (ISMN) retention of the 5-nitrate group and introduction of a series of 2-carbamate functionalities. The compounds proved to be potent and selective inhibitors of human plasma butyrylcholinesterase (huBuChE). In the second group, the nitrate ester was removed and replaced with a variety of alkyl and aryl esters. These generally exhibited nanomolar potency with high selectivity for BuChE over acetylcholinesterase (AChE). The most potent and selective compound was isosorbide-2-benzyl carbamate-5-benzoate with an IC50 of 4.3 nM for BuChE and > 50000 fold selectivity over human erythrocyte AChE. Inhibition with these compounds is time-dependent, competitive, and slowly reversible, indicating active site carbamylation.

Novel bicyclic nucleoside analogues related to natural griseolic acids

Methodologies for the synthesis of novel isomeric nucleosides related to the natural, biologically-active griseolic acids are described. The carbohydrate precursor for the synthesis, 1,4:3,6-dianhydro-D-glucitol, can be prepared easily from D-glucitol.

Selective Esterification of 1,4:3,6-Dianhydro-D-glucitol

Esterification of 1,4:3,6-dianhydro-D-glucitol (1) with carboxylic acids in the presence of 4-dimethylaminopyridine and dicyclohexylcarbodiimide affords 2-exo-acylates 3 with high regioselectivity, in addition to small amounts of the isomeric 5-endo-acylates 4 and 2,5-diacylates 5.

Regioselective Acylation of 1,4:3,6-Dianhydro-D-glucitol

Acylation of 1,4:3,6-dianhydro-D-glucitol with anhydrides in the presence of heavy metal salts affords 5-endo-acylates with high regioselectivity, without detectable amounts of the isomeric 2-acylates.Acyl group migration occurs with preference for the 2-exo-position, on heating an acylation mixture, which contains varying amounts of 1,4:3,6-dianhydro-D-glucitol, 2- and 5-monoacylate and 2,5-diacylate, in the presence of reesterification catalysts and whilst distilling off the lower boiling 2-acylate.