Galactopyranosides reactions

If the ELISA color development takes more than a few minutes, continue the incubation in the dark. P-galactosidase reactions tend to have a lower spontaneous background than peroxidase reactions but the yellow o-nitrophenyl-P-D-galactopyranoside reaction product can take longer to develop, p-galactosidase reactions can be speeded up by incubation at 37°C. 

This indirect method of selective benzoylation at C-4 is of special interest in the galacto series (47). Reaction of methyl 4,6-O-benzylidene-a-D-galactopyranoside 97 with NBS afforded the corresponding 6-bromo-4-benzoate (98) in over 90% yield. The axial hydroxyl group at C-4... 

Direct conversion of the 6-sulfonates of D-galactopyranosides into their 6-deoxy-6-fluoro derivatives is usually hindered, because of the polar field-effect exerted by the lone electron pairs of the axial 0-4 (Ref. 158). Thus, the 6-0-mesylgalactoside 294 gave ° the 3,6-anhydro derivative 297 (23%) as the only isolated product on reaction with CsF in boiling ethanediol. How-... 

Abbreviations All, allyl MP, dimelhylaminopyridine or 2,4,6-trimelhylpyridine MOM, methoxy-methyl Piv, pivaloyl Tr, trityl other abbreviations are the same. Obtained accompanied with the 3,4-0-( methyl orthoacetyl)-a-D-galactoside the 0-deacetyl derivative was also reported. Inserted as a reference reaction. A mixture of two diastereoisomers. On hydrolysis (R = F), 3,6-dideoxy-3,6-difluoro-D-glu-copyranose is formed. Methanolysis gives methyl 3-deoxy-3-fluoro-a-D-galactopyranoside. 

The results of a study of the di- and tri-molar methanesulfonylation of methyl a-D-galactopyranoside suggested, amongst the secondary hydroxyl groups, a reactivity order of HO-2 > HO-3 > HO-4, and, from the latter reaction, the 2,3,6-triester could be isolated in 30% yield a similar reaction of methyl a-D-mannopyranoside gave the... 

Dichloro-4,6-dideoxy-a-D-galactopyranosyl 4,6-dichloro-4,6-dideoxy-a-D-galactopyranoside was obtained in 72% yield by the reaction of a,a-trehalose with sulfuryl chloride.367... 

Selective replacement of primary hydroxyl groups in carbohydrates by iodine atoms has been achieved by using the Rydon reagent, namely, methyltriphenoxyphosphonium iodide.368 Treatment of methyl 3,4-O-isopropylidene-jS-D-galactopyranoside with the phosphonium salt in benzene for 48 hours at room temperature yielded 60% of the 6-deoxy-6-iodo derivative,369 and reaction of thymidine, uridine, and 2,2 -anhydrouridine in N,N-dimethylformamide afforded 5 -deoxy-5 -iodo derivatives in yields of 63, 65, and 31%, respectively.370... 

The reaction of sulfuryl chloride with carbohydrates to give chloro-deoxy derivatives has been reviewed briefly in this Series.98 The reaction of sulfuryl chloride with monosaccharides has been shown to afford products in which the secondary hydroxyl groups are replaced by chlorine with inversion of configuration.68-75 Jones and coworkers reported that the reaction of methyl a-D-glucopyranoside with sulfuryl chloride and pyridine in chloroform at room temperature proceeds by way of the 4,6-bis(chlorosulfate) by an Sn2 process, with chloride as the nucleophile, to give methyl 4,6-dichloro-4,6-dideoxy-a-D-galactopyranoside 2,3-bis(chlorosulfate).74... 

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