Защитные группы в углеводах

Курсовая работа состоит из 52 страниц
Все формулы набраны с помощью программы ChemDraw

Содержание
Введение 3
1. Последние достижения в области региоселективной селективной защиты углеводов 4
2. Использование защитных групп для стереоселективного построения гликозидных связей 7
3. Защита аминогруппы в глюкозамине и его производных 22
4. Защитные группы как визуализационные метки 27
5. Защитные группы в качестве фрагментов облегчающих очистку и выделение 30
Заключение 36
Список сокращений 37
Список литературы 39

1. (a) Wuts G.M. Green’s Protective Groups in Organic Synthesis Fourth Edition / G.M. Wuts, T.W. Greene // J. Wiley & Sons Inc. - 2007. - P. 1110.
(b) Jarowicki K. Protective groups / K. Jarowicki, P. Kocienski // J. Chem. Soc. Perkin Trans. 1. -2001. – Vol. 36. - P. 2109-2135.
(c) Theodoridis G. Nitrogen Protecting Groups: Recent Developments and New Applications / G. Theodoridis // Tetrahedron Lett. – 2000. – № 56. – P. 2339-2358.
(d) Isidro-Llobet A. Amino Acid-Protecting Groups / A. Isidro-Llobet, M. A’lvarez, F. Albericio // J. Chem. Rev. – 2009. – Vol. 109. – P. 2455-2504.
(e) Somoza A. Protecting groups for RNA synthesis: an increasing need for selective preparative methods / A. Somoza // J. Chem. Soc. Rev. – 2008. – Vol. 37. – P.2668-2675.
2. (a) Kamerling J.P. Comprehensive glycoscience, from chemistry to systems biology / J.P.Kamerling, ed. // Oxford. – 2007. – Vol. 1.
(b) Levy D.E. The Organic Chemistry of Sugars / D.E. Levy, P. Fugedi // CRC Press: Boca Raton. – 2006. – P. 181-221.
(c) Protective groups / R.E.J.N. Litjens, L.J. Van den Bos, J.D.C. Code´e, H.S. Overkleeft, G.A. Van der Marel // J. Carbohydr. Res. – 2007. – Vol. 342. – P. 419-429.
3. Zhu X.M. New principles for glycoside-bond formation / X.M. Zhu, R.R. Schmidt // Angew. Chem. Int. – 2009. – Vol. 48. – P. 1900-1934.
4. (a) Regioselective one-pot protection of carbohydrates / C.C. Wang, J.C. Lee, S.Y. Luo, S.S. Kulkarni, Y.W. Huang, C.C. Lee, K.L. Chang, S.C. Hung // Nature. – 2007. – Vol. 446. – P. 896-899.
(b) Regioselective one-pot protection of glucose / C.C. Wang, S.S. Kulkarni, J.C. Lee, S.Y. Luo, S.C. Hung // Nat Protoc. – 2008. - №3. – P. 97-113.
5. (a) Gaunt M.J. Rational Design of Benzyl Protecting Groups Allows Sequential Deprotection of Hydroxyl Groups by Catalytic Hydrogenolysis / M.J. Gaunt, J. Yu, J.B.J. Spencer // J. Org. Chem. – 1998. – Vol. 63. – P. 4172-4173.
(b) Use of 1,2-dichloro 4,5-dicyanoquinone (DDQ) for cleavage of the 2-naphthylmethyl (NAP) group / J. Xia, S.A. Abbas, R.D. Locke, C.F. Piskorz, J.L. Alderfer, K.L. Matta // Tetrahedron Lett. – 2000. – Vol. 41. – P. 169-173.
(c) The 2-Naphthylmethyl (NAP) Group in Carbohydrate Synthesis: First Total Synthesis of the GlyCAM-1 Oligosaccharide Structures / J. Xia, J.L. Alderfer, C.F. Piskorz, K.L. Matta // Chem. Eur. J. – 2001. – Vol. 7. – P. 356-367.
(d) Synthesis of 48 disaccharide building blocks for the assembly of a heparin and heparan sulfate oligosaccharide library / L.D. Lu, C.R. Shie, S.S. Kulkarni, G.R. Pan, X.A. Lu, S.C. Hung // Org. Lett. – 2006. - № 8. – P. 5995-5998.
(e) Vibert A. From polymer to size-defined oligomers: a step economy process for the efficient and stereocontrolled construction of chondroitin oligosaccharides and biotinylated conjugates thereof: part 1 / A. Vibert, C. Lopin-Bon, J.C. Jacquiniet // Chem. Eur. J. – 2009. – Vol. 15. – P. 9561–9578.
6. Français A. Tandem catalysis for a one-pot regioselective protection of carbohydrates: the example of glucose / A. Français, D. Urban, JM. Beau // Angew. Chem. Int. Ed. – 2007. – Vol. 46. – P. 8662-8665.
7. (a) David S. Regioselective manipulation of hydroxyl groups via organotin derivatives / S. David, S. Hanessian // Tetrahedron Lett. – 1985. – Vol. 41. – P. 643-663.
(b) Grindley B.T. Applications of tin-containing intermediates to carbohydrate chemistry / B.T. Grindley // Adv. Carbohydr. Chem. Biochem. – 1998. – Vol. 53. – P. 17-142.
8. Wagner D. Preparation and Synthetic Utility of Some Organotin Derivatives of nucleosides / D. Wagner, J.P.H. Verheyden, J.G. Moffat // J. Org. Chem. – 1974. – Vol. 39. – P. 24-30.
9. Regioselective Protection of Sugars Catalyzed by Dimethyltin Dichloride / Y. Demizu, Y. Kubo, H. Miyosho, T. Maki, Y. Matusumura, N. Moriyama, O. Onomura // Org. Lett. – 2008. - № 10. – P. 5075-5077.
10. (a) Tuning glycoside reactivity: a new tool for efficient oligosaccharide synthesis / N.L. Douglas, S.V. Ley, U. Lücking, S.L. Warriner // J. Chem. Soc., Perkin Trans. 1. – 1998. – P. 51-66.
(b) Koeller K.M. Synthesis of complex carbohydrates and glycoconjugates: Enzyme-based and programmable one-pot strategies / K.M. Koeller, C.H. Wong // J. Chem. Rev. – 2000. – Vol. 100. – P. 4465–4493.
(c) A programmable one-pot oligosaccharide synthesis for diversifying the sugar domains of natural products: A case study of vancomycin / T.K. Ritter, K.K.T. Mong, H.T. Liu, T. Nakatani, C.H. Wong // Angew. Chem. Int. Ed. – 2003. Vol. 42. – P. 4657-4660.
(d) Thioglycosides in sequential glycosylation strategies / J.D.C. Codee, R.E.J.N. Litjens, L.J. van den Bos, H.S. Overkleeft, G.A. van der Marel // J. Chem. Soc. Rev. – 2005. – Vol. 34. – P. 769-782.
(e) Wang Y. Oligosaccharide assembly by one-pot multi-step strategy / Y. Wang, X.S. Ye, L.H. Zhang //J. Org. Biomol. Chem. – 2007. – Vol. 5. – P. 2189-2200.
11. (a) Jensen H.H. Stereochemical Substituent Effects / H.H. Jensen, M. Bols // Acc. Chem. Res. – 2006. – Vol. 39. – P. 259-265.
(b) Jensen H.H. A Fre