5-Hydroxy-3-methyl-2- reduction

Pyrrole has been condensed under alkaline conditions with formaldehyde to give products of either N- or C-hydroxymethylation (Scheme 22). Although acid-catalyzed hydroxy-methylation is not a practical possibility, by addition of a reducing agent to the reaction mixture overall reductive alkylation can be achieved (Scheme 23). 

Chromanone, 3-acetamido-2-methyl-reduction, 3, 729 Chromanone, 3-amino-synthesis, 3, 734 Chromanone, 3-arylidene-thermoisomerization, 3, 722 Chromanone, 3-benzylidene-thermolysis, 3, 728 Chromanone, 3-bromo-2-hydroxy-benzofuran from, 3, 729 Chromanone, 6,8-dimethyl-hydroxymethylation, 3, 731 Chromanone, 2,3-epoxy-as synthon, 3, 735... 

Indazole, 5,5-dimethyl-3-trifluoromethyl-4,5-dihydro-trichomonacidal activity, 5, 291 Indazole, 2-ethoxycarbonyl-reactions, 5, 269 Indazole, 3-fluoro-synthesis, S, 263 Indazole, 1-germyl-synthesis, 5, 236 Indazole, 1-glycosyl-synthesis, 5, 289 Indazole, 2-glycosyl-synthesis, 5, 289 Indazole, halo-reactions, S, 266 Indazole, 2-hydroxy-methylation, 5, 269 Indazole, 3-hydroxy-reactions, S, 264 Indazole, 6-hydroxy-diazo coupling, 5, 86 Indazole, hydroxyphenyl-synthesis, S, 288 Indazole, 3-iodo-synthesis, S, 241 Indazole, l-isopropyl-3-phenyl-reduction, 5, 243 Indazole, 3-mercapto-1 -substituted tautomerism, 5, 265 Indazole, methoxy-... 

Pteridine-6,7-dione, 4-amino-2-chloro-chlorination, 3, 296 Pteridine-6,7-dione, 2,4-dichloro-synthesis, 3, 291 Pteridine-6,7-dione, 5-hydroxy-synthesis, 3, 316 Pteridine-6,7-dione, 8-methyl-reduction, 3, 298 Pteridine-2,6-diones structure, 3, 272 Pteridine-4,6-diones structure, 3, 272 synthesis, 3, 310 Pteridine-6,7-diones reduction, 3, 298 synthesis, 3, 316... 

Saccharin, 2-methyl-reduction, 6, 152 Saccharin, 6-nitro-reduction, 6, 154 Saccharin, thio-hydrolysis, 6, 161 methylation, 6, 160 Safranines applications, 3, 196 Safrole derivatives toxicity, 1, 139-140 occurrence, 6, 781 Safrole, 1-hydroxy-toxicity, 1, 140 Salazosulfapyridine... 

Another attempted synthesis of Tc(III)-EDTA and Tc(III)-HEDTA complexes (EDTA ethylenediaminetetraacetic acid HEDTA A -(2-hydroxy-methyl)ethylenediamine-N,AT, iV -triacetic acid) was carried out using [Tc(tu)6]3+ as the starting complex [40]. Technetium-EDTA complexes have been synthesized by the direct reduction of pertechnetate with a suitable reduc-tant in the presence of excess EDTA [41-43]. On addition of EDTA to the Tc(tu) + solution, the intensity of the absorption spectrum decreased with time and the solution color changed from reddish orange to light brown. An electrophoretic analysis for the Tc(III)-EDTA complex showed that more than 70%... 

Two ciT-dihydroxylation reactions of alkenes formed steps in the synthesis of the antiviral drug (-)-oseltamvir ( tamiflu ) were carried out with RuO /aq. Na(IO )/ EtOAc-CH3CN/4°C [169]. Terminal alkene groups in nucleosides were oxidised to alcohols by RuClj/aq. Na(lO )/EtOAc-CH3CN/0°C thus 3,5-di-0-benzyl-l,2-di-O-isopropylidene-3-C-vinyl-a-D-ribofuranose (1) gave the diol (2) which, on cleavage with Na(lO ) and reduction with NaBH yielded 3,5-di-0-benzyl-l,2-di-O-isopropylidene-3-C-hydroxy-methyl-a-D-ribofuranose (3) (Fig. 3.4) [170]. 

DL-Dihydrostreptose and its ribo isomer were similarly obtained. Birch reduction of 2-methyl-3-furoic acid, followed by addition of methanol, bromination, and dehydrobromination, gave 402 as a mixture of the isomers. Hydroxylation of 402 with osmium tetraoxide-so-dium chlorate, and subsequent treatment with acetone-sulfuric acid afforded three isomeric acetals (403-405). The structures of these compounds were assigned on the basis of their H-n.m.r. spectra. In addition, the relationship between 403 and 404 was established by hydrolysis and reglycosidation. The methyl esters 403-405 were quantitatively reduced to the corresponding alcohols. The mixture of alcohols obtained from 403 and 404 was converted into crystalline 5-deoxy-3-C-(hydroxymethyl)-l,2-0-isopropylidene-a-DL-ribofuran-ose (406), which was compared directly with a sample prepared from D-xylose. Methyl 5-deox y-3-C-(hydroxy methyl)-2,3-O-isopropy lidene-/3-DL-lyxofuranoside (407), obtained by reduction of 405 with lithium aluminum hydride, was hydrolyzed with dilute hydrochloric acid, to give a,/3-DL-dihydrostreptose.2,ifi... 

Such compounds have been identified amongst the products of deamination, followed by reduction, of methyl 2-amino-2-deoxy-a-and -/3-D-glucopyranoside.89a Two methyl 2-deoxy-2-(hydroxy-methyl)pentofuranosides, epimeric at C-2, were detected in each case, and the results of deuterium-incorporation experiments suggested that the primary product was epimerized, probably during reduction with sodium borohydride. However, in the writer s opinion, the configurations assigned to the primary and epimerized products are incorrect and should be reversed. 

Indole, 3-hydroxymethyl-2-phenyl-stability, 4, 272 Indole, l-hydroxy-2-phenyl-synthesis, 4, 363 Indole, 2-iodo-synthesis, 4, 216 Indole, 3-iodo-reactions, 4, 307 synthesis, 4, 216 Indole, 2-iodo-l-methyl-reactions, 4, 307 Indole, 2-lithio-synthesis, 4, 308 Indole, 3-lithio-synthesis, 4, 308 Indole, 2-mercapto-tautomerism, 4, 38, 199 Indole, 3-mercapto-tautomerism, 4, 38, 199 Indole, 3-methoxy-synthesis, 4, 367 Indole, 5-methoxy-oxidatlon, 4, 248 Indole, 7-methoxy-2,3-dimethyl-acetylation, 4, 219 benzoylation, 4, 219 Indole, 5-methoxy-l-methyl-reduction, 4, 256 Indole, 5-methoxy-l-methyl-3-(2-dimethylaminoethyl)-reactions... 

Atorvastatin is a selective, competitive inhibitor of the 3-hydroxy methyl glutaryl coenzyme A (HMG-CoA) reductase enzyme that is involved in the conversion of HMG-CoA to mevalonate (a precursor of sterols, including cholesterol). A reduction of intracellular cholesterol levels... 

Formyl anion equivalent. This reagent can be used as the equivalent of the formyl anion. Thus it reacts with an aldehyde such as 2 in the absence of a catalyst to form mainly the anti-adduct. After protection of the hydroxy group, the thiazole group can be converted to a formyl group by N-methylation, reduction, and hydrolysis. 

Selective reduction of a-hydroxy esters. Reduction of esters with BMS is slow, but can be facilitated by addition of catalytic amounts of sodium borohydride. This method of reduction can be used to effect regioselective reduction of a-hydroxy esters. Thus reduction of dimethyl (S)-( — )-malate (1) results in formation of methyl (3S)-3,4-dihydroxybutanoate (2). 

Hydroxymethyhtion of ketones. A ketone can be converted into the a-hydroxy-methyl derivative in two. steps acylation with ethyl formate, followed by aluminum hydride reduction. The sequence is illustrated for the conversion of 4-rerr-butylcyclo-hcxanone(l) inlo 2-hydroxymelhyl-4-ferf-butylcyclohexanone(3). 

More recently Henglein has shown that Ag(CN)2 is reduced at a low rate by radiolytically generated hydroxy methyl radicals [27e]. It was shown that the reduction is much faster when colloidal silver seed particles are present in the solution, resulting in larger silver particles with a narrow size distribution. The reduction occurs on tiny nuclei formed by hydrolysis in solution. The mechanism proposed here involves CH2OH radicals, which transfer electrons to the seed particles, and the stored electrons reduce the Ag(CN)2 directly on the surface of the seeds. Ag(CN)2 was also shown to be rapidly reduced by the organic radicals in the... 

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