32359-20-9

Usage

Uses

Used in Organic Synthesis:
(1S,2R)-1,2-Dihydroxycyclohexa-3,5-diene-1-carboxylic acid is used as a key intermediate in the synthesis of various organic compounds due to its unique structure and functional groups.
Used in Medicinal Chemistry:
(1S,2R)-1,2-Dihydroxycyclohexa-3,5-diene-1-carboxylic acid is used as a building block for the development of pharmaceuticals, taking advantage of its specific stereochemistry and functional groups to create novel drug candidates with potential therapeutic applications.
Used in Research and Development:
(1S,2R)-1,2-Dihydroxycyclohexa-3,5-diene-1-carboxylic acid serves as an interesting target for chemical research, enabling scientists to explore its properties, reactivity, and potential applications in various chemical and biological processes.

InChI:InChI=1/C7H8O4/c8-5-3-1-2-4-7(5,11)6(9)10/h1-5,8,11H,(H,9,10)/t5-,7+/m1/s1

Upstream product

• 532-32-1 sodium benzoate 
• 65-85-0 benzoic acid 

Downstream Products

• 172877-72-4 (-)-(1S,6R)-methyl 1,6-dihydroxycyclohexa-2,4-dienecarboxylate 
• 1210906-76-5 methyl (1S,6R)-1,6-dihydroxycyclohex-2-enecarboxylate 
• 1310051-99-0 C₈H₁₂O₄ 
• 956264-72-5 (-)-methyl (S)-1-hydroxy-6-oxo-cyclohex-2-encarboxylate 
• 1301703-33-2 (3aS,4R,7S,7aR)-benzyl 4-(benzyloxycarbonylamino)-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-3a-carboxylate 
• 1301703-35-4 (3aS,4R,7S,7aR)-benzyl 7-(benzyloxycarbonylamino)-2,2-dimethyl-4-(4-nitrobenzoyloxy)-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxole-3a-carboxylate 
• 1301703-37-6 benzyl 5-hydroxy-2,2-dimethyl-7-oxohexahydro-3aH-4,8-epoxy[1,3]dioxolo[4',5':5,6]benzo[1,2-d]oxazole-3a-carboxylate 
• 1301703-43-4 (3aR,4R,5R,6R,7S,7aR)-dibenzyl 5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-3a,8-dicarboxylate 
• 1301703-45-6 (3aR,4S,5S,6S,7R,7aS)-dibenzyl 5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate 
• 1301703-41-2 (1R,2R,3S,4R,5R,6R)-3-ammonio-1,2,4,5,6-pentahydroxycyclohexanecarboxylate 
• 1301703-42-3 (1R,2S,3R,4S,5S,6S)-2-carboxy-2,3,4,5,6-pentahydroxycyclohexylammonium chloride 
• 1301703-52-5 (1S,2R,3S,6R)-3-ammonio-1,2,6-trihydroxycyclohexanecarboxylate 
• 1301703-31-0 (3aR,4R,7S,7aR)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)-benzo[d][1,3]dioxole-3a,8-dicarboxylate 
• 1301703-32-1 (3aR,4S,7R,7aS)-dibenzyl 2,2-dimethyl-3a,4,7,7a-tetrahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-7a,8-dicarboxylate 

Relevant academic research and scientific papers

Palladium Catalyzed Stereoselective Arylation of Biocatalytically Derived Cyclic 1,3-Dienes: Chirality Transfer via a Heck-Type Mechanism

Microbial arene oxidation of benzoic acid with Ralstonia eutropha B9 provides a chiral highly functionalized cyclohexadiene, suitable for further structural diversification. Subjecting this scaffold to a Pd-catalyzed Heck reaction effects a regio-and ster

A Chemoenzymatic Formal Synthesis of Epoxyquinols A and B

A formal synthesis of epoxyquinols A and B was completed in nine steps starting from benzoic acid. Enantioselectivity was established through an enzymatic arene dihydroxylation reaction performed by whole cells of Ralstonia eutropha B9 expressing benzoate

A Formal Approach to Xylosmin and Flacourtosides E and F: Chemoenzymatic Total Synthesis of the Hydroxylated Cyclohexenone Carboxylic Acid Moiety of Xylosmin

The hydroxylated cyclohexenone carboxylic acid moiety of xylosmin was synthesized in eight steps from benzoic acid. The key steps in the synthesis involved the enzymatic dihydroxylation of benzoic acid by the whole cell fermentation with Ralstonia eutroph

Chemoenzymatic approach to synthesis of hydroxylated pyrrolidines from benzoic acid

The fermentation of benzoic acid with R. eutrophus B9 provides the corresponding ipso-diol that serves as a convenient homochiral starting material for the synthesis of oxygenated compounds. In this paper we report the conversion of the ipso-diol to a hydroxylated pyrrolidine, which is found as a subunit in biologically active compounds. The key steps involve the enzymatic oxidation of benzoic acid, the subsequent hetero-Diels-Alder cycloaddition, and the oxidative cleavage, reductive cyclization to form the pyrrolizidine. Experimental and spectral data are provided for all new compounds.

Chemoenzymatic synthesis of idesolide from benzoic acid

Idesolide was synthesized in five steps from benzoic acid by base-catalyzed dimerization of hydroxy keto ester, obtained from diol, the product of the whole-cell fermentation of benzoic acid with R. eutrophus B9. Georg Thieme Verlag Stuttgart - New York.

SYNTHESIS OF TETRACYCLINES AND ANALOGUES THEREOF

The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The modular synthesis of tetracyclines and tetracycline analogs described provides an efficient and enantioselective route to a variety of tetracycline analogs and polycyclines previously inaccessible via earlier tetracycline syntheses and semi-synthetic methods. These analogs may be used as anti-microbial agents or anti-proliferative agents in the treatment of diseases of humans or other animals.

Synthesis of a broad array of highly functionalized, enantiomerically pure cyclohexanecarboxylic acid derivatives by microbial dihydroxylation of benzoic acid and subsequent oxidative and rearrangement reactions

(equation presented) We have found that the 1,2-dihydroxylation of benzoic acid with Alcaligenes eutrophus strain B9, first reported in 1971 by Reiner and Hegeman, is readily adapted for the preparation of tens to hundreds of grams of (1S,2R)-1,2-dihydrox

Synthetic application of biotransformations: absolute stereochemistry and Diels-Alder reactions of the (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid from Pseudomonas putida

1,cis-2-Dihydroxycyclohexa-3,5-diene-1-carboxylic acid, 2, produced by Pseudomonas putide, U103, was shown via X-ray analysis of its p-bromobenzoylmethyl ester to have (1S 2R) absolute stereochemistry.The stereo- and regio-selectivity of a series of cycloadditions of the methyl ester 3 (R = Me) the methyl ester acetonide 5 and the hydroxymethylacetonide 6 (R = H) with singlet oxygen, 4-phenyl-4,5-dihydro-3H-1,2,4-triazole-3,5-dione, N-phenylmaleimide and nitrosobenzene have been established.The stereochemistry of the oxygen adduct 7 of 5 was unambiguously assigned by X-ray analysis of 7.The acetonides 5 and 6 (R = H) were attacked by the dienophiles anti to the acetonide group.The diol ester 3 underwent attack on the face syn to the diol groups.The regiochemistry of the addition of nitrosobenzene was predominantly with the N-phenyl group distal to the ester function in 3 and 5, but proximal to the hydroxymethyl group in 6 (R = H).