139013-57-3

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• 127666-06-2 (3aS,7aS)-4-chloro-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 86992-79-2 (1S,2S)-3-Chloro-cyclohexa-3,5-diene-1,2-diol 
• 148132-86-9 (1R,2S,3S,4R,5S,6S)-1-Chloro-3,4-dihydroxy-5,6-di-O-isopropylidene-1,2-epoxycyclohexane 
• 139013-56-2 (1R,4R,5S,6S)-1-chloro-7,8-dioxa-5,6-di-O-isopropylidenebicyclo<2.2.2>oct-2-ene 

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• 123238-09-5 (1R,2R,3S,4R)-cyclohex-5-ene-1,2,3,4-tetrol 

Relevant academic research and scientific papers

Polystyrene-supported N-methylthiourea: A convenient new reagent for the hydrogenolysis of bicyclic endoperoxides

The single-step preparation of a polystyrene-bound N-methylthiourea 4 and its use for the hydrogenolysis of bicyclic endoperoxides is described. The Royal Society of Chemistry 2005.

Synthesis of D-chiro-3-inosose and (+)-D-chiro-inositol

There are described novel biocatalytic and chemical processes for the synthesis of various oxygenated compounds. Particularly, there are described processes for the synthesis of a useful synthon (12) made by reacting a protected diol (acetonide) with permanganate under appropriate conditions. Such synthon is useful of the synthesis of various pharmaceutically important compounds such as D-chiro-inositol and D-chiro-3-inosose. Also, there are disclosed novel compounds, including specifically the synthon (12) and compounds derived therefrom.

Microbial Oxidation of Aromatics in Enantiocontrolled Synthesis. Part 1.Expedient and General Asymmetric Synthesis of Inositols and Carbohydrates via and Unusual Oxidation of a Polarized Diene with Potassium Permanganate

This paper reports on the details of a general design of carbohydrates and cyclitols from biocatalytically derived synthons.Homochiral 1-halogenocyclohexa-4,6-diene-2,3-diols 1a and 1b have been generated from chloro- and bromobenzene, respectively, by means of bacterial dioxygenase of Pseudomonas putida 39D.These chiral synthons have been manipulated to cyclitols and carbohydrates by further stereoselective functionalizations.The preperation of D-chiro-inositol, neo-inositol, muco-inositol, and allo-inositol exemplifies their use in enantiocontrolled synthesis.A novel oxidation of polarized dienes with KMnO4 resulted in the synthesis of α-halogeno epoxy diols, which proved unexpectedly stable.A mechanism is proposed for this transformation and placed in context with the only four reported examples of this reaction in the literature.In addition to the application of this new chemistry to the synthesis of cyclitols, chloro epoxy diol 21a has been transformed into a series of cyclitol synthons by reductive or hydrolytic operations.Reaction of 21a with ammonia led to the preparation of highly oxygenated pyrazines, whose structure were proven by X-ray crystallography.The use of 21a in the preparation of D-chiro-3-inosose, a hitherto unreported cyclitol derivative, is also reported.In addition, chloro epoxy diol 21a was transformed into D-erythruronolactone, completing the synthesis of this important chiral pool reagent in two operations from chlorobenzene.Oxidative cleavage of tetrol 20 yielded D-mannosolactone identical with an authentic sample.

Biocatalysis as a Rational Approach to Enantiodivergent Synthesis of Highly Oxygenated Compounds: (+)- and (-)-Pinitol and Other Cyclitols

Bacterial oxygenation of halogenated aromatic compounds yields arene cis-diols of type 2 of high enantiomeric purity.Further oxygenation of these extremely versatile synthetic intermediates provides for stereo- and regioselective introduction of additional functionalities such as hydroxyl groups.Several rational methods of oxygenation (epoxidation, osmylation, singlet oxygen addition, and ozonolysis) are used to produce, in short synthetic routes, cyclitol derivatives of medicinal importance.Proper symmetry considerations lead to the development of enantiodivergent synthetic design of target compounds from a single enantiomer of a starting diol.These principles are ilustrated on the short syntheses of (+)- and (-)-pinitol.Stereocontrolled oxidative transformation of diols of type 2 are exemplified in the synthesis of conduritol C and dihydroconduritol C.Full experimental details are provided for all compounds.A guide to the stereorational design of any stereoisomer of cyclohexane (poly)ols or carbohydrates is provided at the end of the paper.