ESTUDO DA GLICOSILAÇÃO DO CICLO-HEXANOL COM DIFERENTES DERIVADOS DE D-GLICOSAMINA E PROMOTORES DE GLICOSILAÇÃO PELO MÉTODO DE KOENIGS-KNORR
We report herein a study on the glycosylation of cyclohexanol with four D-glucosamine-based peracetylated glycosyl chlorides bearing different substituents at C-2 and three glycosylation promoters, silver carbonate, silver triflate and mercury II chloride/mercury II oxide, by the Koenigs-Knorr metho...
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Sociedade Brasileira de Química
2016-01-01
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doaj-0a2af330f84a4310b9e34b3f0d4c76b02020-11-24T23:27:01ZengSociedade Brasileira de QuímicaQuímica Nova1678-70642016-01-0139191310.5935/0100-4042.20150174S0100-40422016000100009ESTUDO DA GLICOSILAÇÃO DO CICLO-HEXANOL COM DIFERENTES DERIVADOS DE D-GLICOSAMINA E PROMOTORES DE GLICOSILAÇÃO PELO MÉTODO DE KOENIGS-KNORRLucas L. FrancoWagner G. CanhestroVítor L. S. CunhaJosé D. S. FilhoRicardo J. AlvesWe report herein a study on the glycosylation of cyclohexanol with four D-glucosamine-based peracetylated glycosyl chlorides bearing different substituents at C-2 and three glycosylation promoters, silver carbonate, silver triflate and mercury II chloride/mercury II oxide, by the Koenigs-Knorr method. Under the conditions studied, glycosylation was successful only when 3,4,6-tri-O -acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl chloride was used as the glycosyl donor, with silver carbonate proving the best promoter. In order to investigate the influence of the nature of the halogen at C-1, we also carried out the glycosylation of cyclohexanol with 3,4,6-tri-O -acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl bromide, a more reactive glycosyl donor. As expected, the yield with the bromide derivative was higher with the three promoters and, again, silver carbonate was the most efficient promoter. Finally, to illustrate the well-known efficient procedure for conversion of the phtalimido group at C-2 to the corresponding acetamido group, cyclohexyl 3,4,6-tri-O -acetyl-2-deoxy-2-phtalimido-β-D-glucopyranoside was converted into cyclohexyl 2-deoxy-2-acetamido-β-D-glucopyranoside in two steps, namely, hydrazinolysis of the phtalimido group followed by chemoselective acetylation of the free amino group by treatment with acetic anhydride in methanol, at 77% overall yield.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422016000100009&lng=en&tlng=encyclohexanolN -acetylglucosamineKoenigs-Knorrglycosylation promoters |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Lucas L. Franco Wagner G. Canhestro Vítor L. S. Cunha José D. S. Filho Ricardo J. Alves |
spellingShingle |
Lucas L. Franco Wagner G. Canhestro Vítor L. S. Cunha José D. S. Filho Ricardo J. Alves ESTUDO DA GLICOSILAÇÃO DO CICLO-HEXANOL COM DIFERENTES DERIVADOS DE D-GLICOSAMINA E PROMOTORES DE GLICOSILAÇÃO PELO MÉTODO DE KOENIGS-KNORR Química Nova cyclohexanol N -acetylglucosamine Koenigs-Knorr glycosylation promoters |
author_facet |
Lucas L. Franco Wagner G. Canhestro Vítor L. S. Cunha José D. S. Filho Ricardo J. Alves |
author_sort |
Lucas L. Franco |
title |
ESTUDO DA GLICOSILAÇÃO DO CICLO-HEXANOL COM DIFERENTES DERIVADOS DE D-GLICOSAMINA E PROMOTORES DE GLICOSILAÇÃO PELO MÉTODO DE KOENIGS-KNORR |
title_short |
ESTUDO DA GLICOSILAÇÃO DO CICLO-HEXANOL COM DIFERENTES DERIVADOS DE D-GLICOSAMINA E PROMOTORES DE GLICOSILAÇÃO PELO MÉTODO DE KOENIGS-KNORR |
title_full |
ESTUDO DA GLICOSILAÇÃO DO CICLO-HEXANOL COM DIFERENTES DERIVADOS DE D-GLICOSAMINA E PROMOTORES DE GLICOSILAÇÃO PELO MÉTODO DE KOENIGS-KNORR |
title_fullStr |
ESTUDO DA GLICOSILAÇÃO DO CICLO-HEXANOL COM DIFERENTES DERIVADOS DE D-GLICOSAMINA E PROMOTORES DE GLICOSILAÇÃO PELO MÉTODO DE KOENIGS-KNORR |
title_full_unstemmed |
ESTUDO DA GLICOSILAÇÃO DO CICLO-HEXANOL COM DIFERENTES DERIVADOS DE D-GLICOSAMINA E PROMOTORES DE GLICOSILAÇÃO PELO MÉTODO DE KOENIGS-KNORR |
title_sort |
estudo da glicosilação do ciclo-hexanol com diferentes derivados de d-glicosamina e promotores de glicosilação pelo método de koenigs-knorr |
publisher |
Sociedade Brasileira de Química |
series |
Química Nova |
issn |
1678-7064 |
publishDate |
2016-01-01 |
description |
We report herein a study on the glycosylation of cyclohexanol with four D-glucosamine-based peracetylated glycosyl chlorides bearing different substituents at C-2 and three glycosylation promoters, silver carbonate, silver triflate and mercury II chloride/mercury II oxide, by the Koenigs-Knorr method. Under the conditions studied, glycosylation was successful only when 3,4,6-tri-O -acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl chloride was used as the glycosyl donor, with silver carbonate proving the best promoter. In order to investigate the influence of the nature of the halogen at C-1, we also carried out the glycosylation of cyclohexanol with 3,4,6-tri-O -acetyl-2-deoxy-2-phthalimido-α-D-glucopyranosyl bromide, a more reactive glycosyl donor. As expected, the yield with the bromide derivative was higher with the three promoters and, again, silver carbonate was the most efficient promoter. Finally, to illustrate the well-known efficient procedure for conversion of the phtalimido group at C-2 to the corresponding acetamido group, cyclohexyl 3,4,6-tri-O -acetyl-2-deoxy-2-phtalimido-β-D-glucopyranoside was converted into cyclohexyl 2-deoxy-2-acetamido-β-D-glucopyranoside in two steps, namely, hydrazinolysis of the phtalimido group followed by chemoselective acetylation of the free amino group by treatment with acetic anhydride in methanol, at 77% overall yield. |
topic |
cyclohexanol N -acetylglucosamine Koenigs-Knorr glycosylation promoters |
url |
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422016000100009&lng=en&tlng=en |
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