Efficient one-pot synthesis of 2-hydroxyethyl per-O-acetyl glycosides
-
Hong-Wen Tao
,
Xia Wang
Abstract
A class of stereo-isomerically-pure alkanediol monoglycosides, 2-hydroxyethyl per-O-acetyl pyranosides (IIIa-IIIf), was conveniently prepared by a one-pot reaction of per-O-acetylated pyranoses (Ia-If) and 2-(tert-butyldimethylsilyloxy)ethanol (II) with catalysis by BF3·OEt2. The α-(IIIa) or β-linked glycosides (IIIb-IIIf) with 1,2-trans-configuration were obtained from glycosyl donors with participation of the neighbouring 2-O-acetyl group. BF3·OEt2, along with hydrogen fluoride released from BF3·OEt2 under the experimental conditions used, facilitates the subsequent de-protection of siloxane to successfully afford 2-hydroxyethyl per-O-acetyl-pyranosides.
[1] Baldwin, A. D., & Kiick, K. L. (2010). Polysaccharide-modified synthetic polymeric biomaterials. Peptide Science, 94, 128–140. DOI: 10.1002/bip.21334. http://dx.doi.org/10.1002/bip.2133410.1002/bip.21334Search in Google Scholar
[2] Camponovo, J., Hadad, C., Ruiz, J., Cloutet, E., Gatard, S., Muzart, J., Bouquillon, S., & Astruc, D. (2009). “Click” glycodendrimers containing 27, 81, and 243 modified xylopyranoside termini. Journal of Organic Chemistry, 74, 5071–5074. DOI: 10.1021/jo900554b. http://dx.doi.org/10.1021/jo900554b10.1021/jo900554bSearch in Google Scholar
[3] Chérigo, L., Pereda-Miranda, R., Fragoso-Serrano, M., Jacobo-Herrera, N., Kaatz, G.W., & Gibbons, S. (2008). Inhibitors of bacterial multidrug efflux pumps from the resin glycosides of Ipomoea murucoides. Journal of Natural Products, 71, 1037–1045. DOI: 10.1021/np800148w. http://dx.doi.org/10.1021/np800148w10.1021/np800148wSearch in Google Scholar
[4] Dahmén, J., Frejd, T., Magnusson, G., & Noori, G. (1983). Boron trifluoride etherate-induced glycosidation: formation of alkyl glycosides and thioglycosides of 2-deoxy-2-phthalimidoglycopyranoses. Carbohydrate Research, 114, 328–330. DOI: 10.1016/0008-6215(83)88202-0. http://dx.doi.org/10.1016/0008-6215(83)88202-010.1016/0008-6215(83)88202-0Search in Google Scholar
[5] Enes, R. F., Tomé, A. C., Cavaleiro, J. A. S., El-Agamey, A., & McGarvey, D. J. (2005). Synthesis and solvent dependence of the photophysical properties of [60]fullerene-sugar conjugates. Tetrahedron, 61, 11873–11881. DOI: 10.1016/j.tet.2005.09.078. http://dx.doi.org/10.1016/j.tet.2005.09.07810.1016/j.tet.2005.09.078Search in Google Scholar
[6] Ferrier, R. J., & Hatton, L. R. (1968). Studies with radioactive sugars: Part I. Aspects of the alcoholysis of d-xylose and d-glucose; the role of the acyclic acetals. Carbohydrate Research, 6, 75–86. DOI: 10.1016/s0008-6215(00)80060-9. http://dx.doi.org/10.1016/S0008-6215(00)80060-910.1016/S0008-6215(00)80060-9Search in Google Scholar
[7] Hanessian, S., & Banoub, J. (1977). Chemistry of the glycosidic linkage. O-glycosylations catalyzed by stannic chloride, in the d-ribofuranose and d-glucopyranose series. Carbohydrate Research, 57, 261–267. DOI: 10.1016/s0008-6215(00)83314-5. http://dx.doi.org/10.1016/S0008-6215(00)83314-510.1016/S0008-6215(00)83314-5Search in Google Scholar
[8] Hayes, W., Osborn, H. M. I., Osborne, S. D., Rastall, R. A., & Romagnoli, B. (2003). One-pot synthesis of multivalent arrays of mannose mono- and disaccharides. Tetrahedron, 59, 7983–7996. DOI: 10.1016/j.tet.2003.08.011. http://dx.doi.org/10.1016/j.tet.2003.08.01110.1016/j.tet.2003.08.011Search in Google Scholar
[9] Joshi, V. Y., & Sawant, M. R. (2007). Novel stereo controlled glycosylation of 1,2,3,4,6-penta-O-acetyl-β-d-glucopyranoside using MgO-ZrO2 as an environmentally benign catalyst. Catalysis Communications, 8, 1910–1916. DOI: 10.1016/j.catcom.2007.03.010. http://dx.doi.org/10.1016/j.catcom.2007.03.01010.1016/j.catcom.2007.03.010Search in Google Scholar
[10] Katajisto, J., Virta, P., & Lönnberg, H. (2004). Solid-phase synthesis of multiantennary oligonucleotide glycoconjugates utilizing on-support oximation. Bioconjugate Chemistry, 15, 890–896. DOI: 10.1021/bc049955n. http://dx.doi.org/10.1021/bc049955n10.1021/bc049955nSearch in Google Scholar PubMed
[11] Katsuraya, K., Ikushima, N., Takahashi, N., Shoji, T., Nakashima, H., Yamamoto, N., Yoshida, T., & Uryu, T. (1994). Synthesis of sulfated alkyl malto- and laminara-oligosaccharides with potent inhibitory effects on AIDS virus infection. Carbohydrate Research, 260, 51–61. DOI: 10.1016/0008-6215(94)80021-9. http://dx.doi.org/10.1016/0008-6215(94)80021-910.1016/0008-6215(94)80021-9Search in Google Scholar
[12] Koto, S., Morishima, N., Kawahara, R., Ishikawa, K., & Zen, S. O. (1982). A study of the rapid anomerization of poly-O-benzyl-β-d-glucopyranosides with titanium tetrachloride. Bulletin of the Chemical Sociaty of Japan, 55, 1092–1096. DOI: 10.1246/bcsj.55.1092. http://dx.doi.org/10.1246/bcsj.55.109210.1246/bcsj.55.1092Search in Google Scholar
[13] Lucas, R., Gómez-Pinto, I., Aviñó, A., Reina, J. J., Eritja, R., González, C., & Morales, J. C. (2011). Highly polar carbohydrates stack onto DNA duplexes via CH/π interactions. Journal of the American Chemical Society, 133, 1909–1916. DOI: 10.1021/ja108962j. http://dx.doi.org/10.1021/ja108962j10.1021/ja108962jSearch in Google Scholar
[14] Mukthavaram, R., Marepally, S., Venkata, M. Y., Vegi, G. N., Sistla, R., & Chaudhuri, A. (2009). Cationic glycolipids with cyclic and open galactose head groups for the selective targeting of genes to mouse liver. Biomaterials, 30, 2369–2384. DOI: 10.1016/j.biomaterials.2008.12.074. http://dx.doi.org/10.1016/j.biomaterials.2008.12.07410.1016/j.biomaterials.2008.12.074Search in Google Scholar
[15] Nicolaou, K. C., & Mitchell, H. J. (2001). Adventures in carbohydrate chemistry: new synthetic technologies, chemical synthesis, molecular design, and chemical biology. Angewandte Chemie International Edition, 40, 1576–1624. DOI: 10.1002/1521-3773(20010504)40:9〈1576::aid-anie15760〉3.0.co;2-g. http://dx.doi.org/10.1002/1521-3773(20010504)40:9<1576::AID-ANIE15760>3.0.CO;2-G10.1002/1521-3773(20010504)40:9<1576::AID-ANIE15760>3.0.CO;2-GSearch in Google Scholar
[16] Paulsen, H., & Paal, M. (1984). Lewissäure-katalysierte Synthesen von Di- und Trisaccharid-sequenzen der O- und N-Glycoproteine. Anwendung von Trimethylsilyltrifluoromethanesulfonat. Carbohydrate Research, 135, 53–69. DOI: 10.1016/0008-6215(84)85005-3. (in German) http://dx.doi.org/10.1016/0008-6215(84)85005-310.1016/0008-6215(84)85005-3Search in Google Scholar
[17] Pereda-Miranda, R., & Bah, M. (2003). Biodynamic constituents in the Mexican morning glories: Purgative remedies transcending boundaries. Current Topics in Medicinal Chemistry, 3, 111–131. DOI: 10.2174/1568026033392534. http://dx.doi.org/10.2174/156802603339253410.2174/1568026033392534Search in Google Scholar
[18] Petrig, J., Schibli, R., Dumas, C., Alberto, R., & Schubiger, P. A. (2001). Derivatization of glucose and 2-deoxyglucose for transition metal complexation: Substitution reactions with organometallic 99mTc and Re precursors and fundamental NMR investigations. Chemistry — A European Journal, 7, 1868–1873. DOI: 10.1002/1521-3765(20010504)7:9〈1868::aid-chem1868〉3.0.co;2-h. http://dx.doi.org/10.1002/1521-3765(20010504)7:9<1868::AID-CHEM1868>3.0.CO;2-H10.1002/1521-3765(20010504)7:9<1868::AID-CHEM1868>3.0.CO;2-HSearch in Google Scholar
[19] Sorg, B. L., Hull, W. E., Kliem, H. C., Mier, W., & Wiessler, M. (2005). Synthesis and NMR characterization of hydroxyurea and mesylglycol glycoconjugates as drug candidates for targeted cancer chemotherapy. Carbohydrate Research, 340, 181–189. DOI: 10.1016/j.carres.2004.11.024. http://dx.doi.org/10.1016/j.carres.2004.11.02410.1016/j.carres.2004.11.024Search in Google Scholar
[20] Thoma, G., Magnani, J. L., Patton, J. T., Ernst, B., & Jahnke, W. (2001). Preorganization of the bioactive conformation of sialyl Lewisx analogues correlates with their affinity to E-selectin. Angewandte Chemie International Edition, 40, 1941–1945. DOI: 10.1002/1521-3773(20010518)40:10〈1941:: aid-anie1941〉3.0.co;2-t. http://dx.doi.org/10.1002/1521-3773(20010518)40:10<1941::AID-ANIE1941>3.0.CO;2-T10.1002/1521-3773(20010518)40:10<1941::AID-ANIE1941>3.0.CO;2-TSearch in Google Scholar
[21] Tsuzuki, M., & Tsuchiya, T. (1998). Synthesis of α,α-, α,β-, and β,β-(dimaltoside)s of ethane-1,2-diol, propane-1,3-diol, and butane-1,4-diol: A proposal for an initial adhesion mode. Carbohydrate Research, 311, 11–24. DOI: 10.1016/s0008-6215(98)00191-8. http://dx.doi.org/10.1016/S0008-6215(98)00191-810.1016/S0008-6215(98)00191-8Search in Google Scholar
[22] Wang, S. S., Liu, D., Zhang, X., Li, S. G., Sun, Y. X., Li, J., Zhou, Y. F., & Zhang, L. P. (2007). Study on glycosylated prodrugs of toxoflavins for antibody-directed enzyme tumor therapy. Carbohydrate Research, 342, 1254–1260. DOI: 10.1016/j.carres.2007.03.006. http://dx.doi.org/10.1016/j.carres.2007.03.00610.1016/j.carres.2007.03.006Search in Google Scholar PubMed
[23] Woo, Y. H., Fernandes, R. P., & Proteau, P. J. (2006). Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy-d-xylulose 5-phosphate reductoisomerase. Bioorganic & Medicinal Chemistry, 14, 2375–2385. DOI: 10.1016/j.bmc.2005.11.012. http://dx.doi.org/10.1016/j.bmc.2005.11.01210.1016/j.bmc.2005.11.012Search in Google Scholar PubMed
[24] Wulff, G., & Röhle, G. (1974). Results and problems of Oglycoside synthesis. Angewandte Chemie International Edition, 13, 157–170. DOI: 10.1002/anie.197401571. http://dx.doi.org/10.1002/anie.19740157110.1002/anie.197401571Search in Google Scholar PubMed
[25] Yu, W. Y., Zhang, N., & Li, C. J. (2009). Saccharide modified pharmaceutical nanocarriers for targeted drug and gene delivery. Current Pharmaceutical Design, 15, 3826–3836. DOI: 10.2174/138161209789649547. http://dx.doi.org/10.2174/13816120978964954710.2174/138161209789649547Search in Google Scholar PubMed
[26] Zhou, L., Yang, H. S., & Wang, P. F. (2011). Development of trityl-based photolabile hydroxyl protecting groups. Journal of Organic Chemistry, 76, 5873–5881. DOI: 10.1021/jo200692c. http://dx.doi.org/10.1021/jo200692c10.1021/jo200692cSearch in Google Scholar PubMed
© 2014 Institute of Chemistry, Slovak Academy of Sciences
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Articles in the same Issue
- Recent advances in application of liquid-based micro-extraction: A review
- Determination of nitrites and nitrates in drinking water using capillary electrophoresis
- Comparison of digestion methods for determination of total phosphorus in river sediments
- Interdisciplinary study on pottery experimentally impregnated with wine
- Improvement in γ-decalactone production by Yarrowia sp. after genome shuffling
- Development of an effective extraction process for coenzyme Q10 from Artemia
- Effect of anions on the structure and catalytic properties of a La-doped Cu-Mn catalyst in the water-gas shift reaction
- Effect of apple pomace powder addition on farinographic properties of wheat dough and biscuits quality
- Influence of caffeine and temperature on corrosion-resistance of CoCrMo alloy
- Cetyltrimethylammonium bromide- and ethylene glycol-assisted preparation of mono-dispersed indium oxide nanoparticles using hydrothermal method
- Sol-gel synthesis, characterisation, and photocatalytic activity of porous spinel Co3O4 nanosheets
- Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate
- Potassium phthalimide-catalysed one-pot multi-component reaction for efficient synthesis of amino-benzochromenes in aqueous media
- Organocatalytic SOMO reactions of copper(I)-acetylide and alkylindium compounds with aldehydes
- Molecular modelling and quantitative structure-activity relationship studies of anatoxin-a and epibatidine derivatives with affinity to rodent nAChR receptors
- Efficient one-pot synthesis of 2-hydroxyethyl per-O-acetyl glycosides
- Properties of singlet- and triplet-excited states of hemicyanine dyes
