86992-79-2Relevant academic research and scientific papers
Concise chemoenzymatic synthesis of methyl d-2,3-dideoxyriboside
Ramos, Juan C.,Bracco, Paula,Mazzini, Mauro,Fernandez, Jose R.,Gamenara, Daniela,Seoane, Gustavo A.
scheme or table, p. 969 - 972 (2010/08/07)
The synthesis of methyl α- and β-d-2,3-dideoxyriboside from a non-carbohydrate source is presented. The source of chirality is the microbial oxidation of halobenzenes to produce cyclohexadienediols, which are transformed into the final product in five steps with high chemical and enantiomeric purity.
Medium-scale preparation of useful metabolites of aromatic compounds via whole-cell fermentation with recombinant organisms
Endoma, Mary Ann,Bui, Vu P.,Hansen, Jeff,Hudlicky, Tomas
, p. 525 - 532 (2013/09/06)
The whole-cell fermentation of aromatic coumpounds with Escherichia coli JM109 (pDTG601) on a medium scale (10-15L) produces enantiopure cyclohexadienediols. A detailed procedure for the fermentation is described, and yields for several metabolites are provided. A similar procedure using E. coli JM109 (pDTG602) affords catechols. The dienediols are useful for asymmetric synthesis, and several important targets originating from these metabolites are tabulated.
Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes
Boyd, Derek R.,Sharma, Narain D.,Byrne, Breige,Hand, Mark V.,Malone, John F.,Sheldrake, Gary N.,Blacker, John,Dalton, Howard
, p. 1935 - 1943 (2007/10/03)
Toluene dioxygenase-catalysed oxidation of mono-substituted benzene substrates (R = F, Cl, Br, I, Me, Et, CH2OAc, CH=CH2, C=CH, CF3, CN, OMe, OEt, SMe) in growing cultures of Pseudomonas putida UV4 yielded the corresponding cis-dihydrodiol metabolites. Palladium-catalysed cross-coupling of cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene with a range of tributyltin compounds provided a chemoenzymatic route to a further series of cis-dihydrodiol derivatives of monosubstituted benzenes (R = D, CH2CH=CH2, Bun, SEt, SPr1, SBu1, SPh, SC6H4Me-4). The enantiopurities and absolute configurations of the cis-dihydrodiols, obtained by both enzymatic and chemoenzymatic routes, were determined by several new methods including 1H NMR spectroscopic analysis of the bis-MTPA esters of the 4-phenyl-1,2,4-triazoline-3,5-dione cycloadducts, X-ray crystallography, circular dichroism spectroscopy and stereochemical correlation.
Enantioselective Bacterial Biotransformation Routes to cis-Diol Metabolites of Monosubstituted Benzenes, Naphthalene and Benzocycloalkenes of Either Absolute Configuration
Allen, Christopher C. R.,Boyd, Derek R.,Dalton, Howard,Sharma, Narain D.,Brannigan, Ian,et al.
, p. 117 - 118 (2007/10/02)
Enzyme-catalysed kinetic resolution and asymmetric dihydroxylation routes to enantiopure cis-diol metabolites of arenes and benzocycloalkenes of either absolute configuration have been developed using appropriate strains of the bacterium Pseudomonas putida.
Enantiospecific and Stereoselective Synthesis of (-)-Conduritol C from Chlorobenzene via Microbial Oxidation and Epoxidation
Carless, Howard A. J.
, p. 234 - 235 (2007/10/02)
A four-step route to (-)-conduritol C 1 is described, via the enantiospecific conversion of chlorobenzene to the diene cis-diol 7 and subsequent cis-epoxidation to yield 8.
AN ENANTIODIVERGENT APPROACH TO D- AND L-ERYTHROSE VIA MICROBIAL OXIDATION OF CHLOROBENZENE
Hudlicky, Tomas,Luna, Hector,Price, John D.,Rulin, Fan
, p. 4053 - 4054 (2007/10/02)
D- and L-erythrose derivatives have been synthesized from chlorobenzene, providing for the conversion of undesired pollutants to synthetically useful chiral intermediates.The overall yields of the title compounds are compared to known preparation from ara
