150767-96-7

Usage

Uses

Used in Pharmaceutical Industry:
(+)-CIS-2(R),3(S)-2,3-DIHYDROXY-2,3-DIHYDROBENZONITRILE ACETONIDE is used as a building block for the synthesis of various pharmaceuticals and biologically active compounds. Its unique structure and properties make it a valuable component in drug development and research.
Further studies are needed to fully understand its potential uses and benefits in the pharmaceutical field.

Upstream product

• 138769-96-7 (5S,6R)-5,6-dihydroxycyclohexa-1,3-dienecarbonitrile 
• 77-76-9 2,2-dimethoxy-propane 
• 100-47-0 benzonitrile 

Relevant academic research and scientific papers

Aza and oxo Diels-Alder reactions using cis-cyclohexadienediols of microbial origin: Chemoenzymatic preparation of synthetically valuable heterocyclic scaffolds

Aza and oxo Diels-Alder reactions using enantiopure cis-cyclohexadienediols were studied. These dienediols were obtained from the biotransformation of monosubstituted arenes using bacterial dioxygenases (toluene and benzoate dioxygenases). Ethyl glyoxylate and its N-tosyl imine were used as dienophiles to afford the corresponding hetero Diels-Alder bicyclic adducts with excellent regio- and stereoselectivities. Quantum chemical calculations at the B3LYP/6-31+G(d,p) level of theory were performed to rationalize the observed selectivities especially the stereochemical aspects of the cycloadditions. The synthetic importance of these adducts is highlighted for the preparation of enantiopure 2,2,3,4,5,6-hexasubstituted piperidine and tetrahydropyran from toluene.

Synthesis of (-)-6-hydroxyshikimic acid from ((5S,6R)-5,6-dihydroxy-1,3-cyclohexadienyl)methanenitrile

A six step synthesis of (-)-6-hydroxyshikimic acid 2 has been developed starting from ((5S,6R)-5,6-dihydroxy-1,3-cyclohexadienyl)methanenitrile 3, produced by biotransformation of cyanobenzene by the enzyme toluene dioxygenase.

Enantiospecific synthesis of cyanocyclitols and (6R)-6-hydroxyshikimic acid from benzonitrile

The chiral cis-3-cyanocyclohexa-3,5-diene-1,2-diol 5, available by microbial oxidation of benzonitrile, is the key intermediate used in brief syntheses of the cyanocyclitols 9 and 15, and in the synthesis of 6-hydroxyshikimic acid 20.

Syntheses of 6β-hydroxyshikimic acid and its derivatives

The conversion of (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol, (5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carbonitrile and methyl (5S,6S)-5,6-dihydroxycyclohexa-1,3-diene-1-carboxylate into 6β-hydroxyshikimic acid and protected derivatives is described.