I2-mediated α-selective Ferrier glycosylation approach to synthesis of O-glycosyl amino acids
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Li Ren
,
Yang Liu
Abstract
I2 is an effective promoter for the synthesis of 2,3-unsaturated glycosides via Ferrier glycosylation. This reaction was used in the present work for the synthesis of O-glycosylated Fmoc amino acid building blocks. This metal-free reaction afforded the desired products with good to excellent yields with good α-selectivity.
[1] Bertozzi, C. R., & Kiessling, L. L. (2001). Chemical glycobiology. Science, 291, 2357–2364. DOI: 10.1126/science.1059820. http://dx.doi.org/10.1126/science.105982010.1126/science.1059820Suche in Google Scholar
[2] Collins, P. C., & Ferrier, R. J. (1995). Monosaccharides: Their chemistry and their roles in natural products. Chichester, UK: Wiley. Suche in Google Scholar
[3] Dwek, R. A. (1996). Glycobiology: Toward understanding the function of sugars. Chemical Reviews, 96, 683–720. DOI: 10.1021/cr940283b. http://dx.doi.org/10.1021/cr940283b10.1021/cr940283bSuche in Google Scholar
[4] Franz, A. H., Wei, Y. Q., Samoshin, V. V., & Gross, P. H. (2002). Mild synthesis of disaccharidic 2,3-enopyranosyl cyanides and 2-C-2-deoxy pyranosyl cyanides with Hg(CN)2/HgBr2/TMSCN. The Journal of Organic Chemistry, 67, 7662–7669. DOI: 10.1021/jo0111661. http://dx.doi.org/10.1021/jo011166110.1021/jo0111661Suche in Google Scholar
[5] Halkes, K. M., Gotfredsen, C. H., Grøtli, M., Miranda, L. P., Duus, J. Ø, & Meldal, M. (2001). Solid-phase glycosylation of peptide templates and on-bead MAS-NMR analysis: Perspectives for glycopeptide libraries. Chemistry — A European Journal, 7, 3584–3591. DOI: 10.1002/1521-3765(20010817)7:16<3584::AID-CHEM3584>3.0.CO;2-Z. http://dx.doi.org/10.1002/1521-3765(20010817)7:16<3584::AID-CHEM3584>3.0.CO;2-Z10.1002/1521-3765(20010817)7:16<3584::AID-CHEM3584>3.0.CO;2-ZSuche in Google Scholar
[6] Herzner, H., Reipen, T., Schultz, M., & Kunz, H. (2000). Synthesis of glycopeptides containing carbohydrate and peptide recognition motifs. Chemical Reviews, 100, 4495–4538. DOI: 10.1021/cr990308c. http://dx.doi.org/10.1021/cr990308c10.1021/cr990308cSuche in Google Scholar
[7] Hoffmann, H. M. R., Herden, U., Breithor, M., & Rhode, O. (1997). Polyannulated glycopyranosides via radical-mediated tandem reactions. Stereoselective synthesis of 6·5·6 dioxatricycles via 5-exo-trig, 6-endo-dig mode — III. Tetrahedron, 53, 8383–8400. DOI: 10.1016/s0040-4020(97)00518-8. http://dx.doi.org/10.1016/S0040-4020(97)00518-810.1016/S0040-4020(97)00518-8Suche in Google Scholar
[8] Jensen, K. J., Meldal, M., & Bock, K. (1993). Glycosylation of phenols: preparation of 1,2-cis and 1,2-trans glycosylated tyrosine derivatives to be used in solid-phase glycopeptide synthesis. Journal of the Chemical Society, Perkin Transactions 1, 1993, 2119–2129. DOI: 10.1039/p19930002119. http://dx.doi.org/10.1039/p1993000211910.1039/p19930002119Suche in Google Scholar
[9] Kihlberg, J., & Elofsson, M. (1997). Solid-phase synthesis of glycopeptides: Immunological studies with T cell stimulating glycopeptides. Current Medicinal Chemistry, 4, 85–116. 10.2174/0929867304666220309204820Suche in Google Scholar
[10] Kunz, H. (1987). Synthesis of glycopeptides, partial structures of biological recognition components [New synthetic methods (67)]. Angewandte Chemie International Edition in English, 26, 294–308. DOI: 10.1002/anie.198702941. http://dx.doi.org/10.1002/anie.19870294110.1002/anie.198702941Suche in Google Scholar
[11] Lemieux, R. U., & Ratcliffe, R. M. (1979). The azidonitration of tri-O-acetyl-D-galactal. Canadian Journal of Chemistry, 57, 1244–1251. DOI: 10.1139/v79-203. http://dx.doi.org/10.1139/v79-20310.1139/v79-203Suche in Google Scholar
[12] Mitchell, S. A., Pratt, M. R., Hruby, V. J., & Polt, R. (2001). Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin. The Journal Organic Chemistry, 66, 2327–2342. DOI: 10.1021/jo005712m. http://dx.doi.org/10.1021/jo005712m10.1021/jo005712mSuche in Google Scholar
[13] Rudd, P. M., Elliott, T., Cresswell, P., Wilson, I. A., & Dwek, R. A. (2001). Glycosylation and the immune system. Science, 291, 2370–2376. DOI: 10.1126/science.291.5512.2370. http://dx.doi.org/10.1126/science.291.5512.237010.1126/science.291.5512.2370Suche in Google Scholar
[14] Schleyer, A., Meldal, M., Manat, R., Paulsen, H., & Bock, K. (1997). Direct solid-phase glycosylations of peptide templates on a novel PEG-based resin. Angewandte Chemie International Edition in English, 36, 1976–1978. DOI: 10.1002/anie.199719761. http://dx.doi.org/10.1002/anie.19971976110.1002/anie.199719761Suche in Google Scholar
[15] St. Hilaire, P. M., Lowary, T. L., Meldal, M., & Bock, K. (1998). Oligosaccharide mimetics obtained by novel, rapid screening of carboxylic acid encoded glycopeptide libraries. Journal of the Americal Chemical Society, 120, 13312–13320. DOI: 10.1021/ja980387u. http://dx.doi.org/10.1021/ja980387u10.1021/ja980387uSuche in Google Scholar
[16] Subba Reddy, B. V., Divyavania, C., & Yadav, J. S. (2010). Highly stereoselective synthesis of 2,3-unsaturated thiogly-copyranosides employing molecular iodine. Synthesis, 2010, 1617–1620. DOI: 10.1055/s-0029-1218722. http://dx.doi.org/10.1055/s-0029-121872210.1055/s-0029-1218722Suche in Google Scholar
[17] Talbot, P., Shur, B. D., & Myles, D. G. (2003). Cell adhesion and fertilization: Steps in oocyte transport, sperm-zona pellucida interactions, and sperm-egg fusion. Biology of Reproduction, 68, 1–9. DOI: 10.1095/biolreprod.102.007856. http://dx.doi.org/10.1095/biolreprod.102.00785610.1095/biolreprod.102.007856Suche in Google Scholar
[18] Tsuda, T., & Nishimura, S. I. (1996). Synthesis of an antifreeze glycoprotein analogue: efficient preparation of sequential glycopeptide polymers. Chemical Communications, 1996, 2779–2780. DOI: 10.1039/cc9960002779. http://dx.doi.org/10.1039/cc996000277910.1039/cc9960002779Suche in Google Scholar
[19] van Ameijde, J. V., Albadaa, H. B., & Liskamp, R. M. J. (2002). A convenient preparation of several N-linked glycoamino acid building blocks for efficient solid-phase synthesis of glycopeptides. Journal of the Chemical Society, Perkin Transactions 1, 2002, 1042–1049. DOI: 10.1039/b201296k. http://dx.doi.org/10.1039/b201296k10.1039/b201296kSuche in Google Scholar
[20] Varki, A. (1993). Biological roles of oligosaccharides: All of the theories are correct. Glycobiology, 3, 97–130. DOI: 10.1093/glycob/3.2.97. http://dx.doi.org/10.1093/glycob/3.2.9710.1093/glycob/3.2.97Suche in Google Scholar
[21] Wang, Z. G., Zhang, X. F., Live, D., & Danishefsky, S. J. (2000). From glycals to glycopeptides: A convergent and stereoselective total synthesis of a high mannose N-linked glycopeptide. Angewandte Chemie International Edition, 39, 3652–3656. DOI: 10.1002/1521-3773(20001016)39:20<3652::AIDANIE3652>3.0.CO;2-B. http://dx.doi.org/10.1002/1521-3773(20001016)39:20<3652::AID-ANIE3652>3.0.CO;2-B10.1002/1521-3773(20001016)39:20<3652::AID-ANIE3652>3.0.CO;2-BSuche in Google Scholar
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