D-Rybono-1,4-lakton. Część 1, Otrzymywanie i wybrane pochodne

• Autorzy: Madaj J. , Samaszko-Fiertek J. , Ślusarz R. , Dmochowska B.

Warianty tytułu

EN

D-Ribono-1,4-lactone. Part 1, Preparation and seleced derivatives

• Języki publikacji: PL

Abstrakty

EN

Sugars are extremely important chiral substrates in organic synthesis. Thanks to the possibility of obtaining them from natural sources, their prices are relatively low which increases their attractiveness. d-Ribono-1,4-lactone is included in these compounds. For years it has enjoyed great interest as a substrate. In the early 1980’s two review articles were published in reputable journals [4, 5]. It has been a long time since these articles were published so we have decided to prepare a more up- -to-date review article in Polish. d-Ribono-1,4-lactone can be synthesized in many ways. The most interesting way seems to be the oxidation with KMnO₄ [9] or molecular Br₂ [10]. The use of bromine may appear to be harmful to the environment. That is why the search for more environmentally friendly methods is ongoing. However, the new methods are not as sufficiently satisfactory and often more expensive than the conventional, previously named methods. Therefore, the most commonly used method is the oxidation of D-ribose with molecular bromine. Very important derivatives of d-ribonolactone are acetal derivatives: 2,3-O-isopropylidene [10, 16] and 3,4-O-benzylidene derivatives [17]. They are often the starting materials for further synthesis. In the case of the latter compound the proper structure was determined by crystallography many years after its synthesis [18]. Very important group of derivatives are derivatives modificated at C-5: sulphonic [21], fluorine [22], chlorine [23], bromine [16, 24], azide [25] and phosphate [27]. Especially important are 5-bromo-5-deoxy derivatives. Examples of their use for the synthesis of thioalditols and thiosugars are described in the literature. It is also worth mentioning the possibility of synthesis of 1,2-unsaturated [28–30] and 2,3-unsaturated [31] derivatives. Presented examples of derivatives prove that using a d-ribono-1,4-lactone a whole range of derivatives extremely useful for further synthesis of more complex compounds can be obtained.

Słowa kluczowe

PL

D-ribono-1,4-lactone; otrzymywanie; wybrane pochodne

EN

D-Ribono-1,4-lactone; preparation; seleced derivatives

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2017
• Tom: [Z] 71, 11-12
• Strony: 844--859
• Opis fizyczny: Bibliogr. 34 poz., schem.

Twórcy

autor

Madaj J.

• Wydział Chemii Uniwersytetu Gdańskiego,ul. Wita Stwosza 63, 80-308 Gdańsk

autor

Samaszko-Fiertek J.

• Wydział Chemii Uniwersytetu Gdańskiego,ul. Wita Stwosza 63, 80-308 Gdańsk

autor

Ślusarz R.

• Wydział Chemii Uniwersytetu Gdańskiego,ul. Wita Stwosza 63, 80-308 Gdańsk

autor

Dmochowska B.

• Wydział Chemii Uniwersytetu Gdańskiego,ul. Wita Stwosza 63, 80-308 Gdańsk

Bibliografia

• [1] A.S. Eustáquio, R.P. McGlinchey, Y. Liu, Ch. Hazzard, L.L. Beer, G. Florova, M.M. Alhamadsheh, A. Lechner, A.J. Kale, Y. Kobayashi, K.A. Reynolds, B.S. Moore, PNAS, 2009, 106, 12295.
• [2] A.J. Kale, R.P. McGlinchey, B.S. Moore, J. Biol. Chem., 2010, 285, 33710.
• [3] A. Sengupta, A. Basant, S. Ghosh, S. Sharma, H.M. Sonawat, J. Parasitol. Res., 2011, 1.
• [4] S.-Y. Chen, M.M. Joullié, Tetrahedron Lett., 1983, 24, 5027.
• [5] S.-Y. Chen, M.M. Joullié, J. Org. Chem., 1984, 49, 2168.
• [6] M. Steiger, Helv. Chim. Acta, 1936, 19, 189.
• [7] R. Weimberg, J. Biol. Chem., 1961, 236, 629.
• [8] S. Morgenlie, Acta Chem. Scand., 1973, 27, 2607.
• [9] B. Kaskar, G.L. Heise, R.S. Michalak, B.R. Vishnuvajjala, Synthesis, 1990, 1990(11), 1031.
• [10] J.D. Williams, V.P. Kamath, P.E. Morris, L.B. Townsend, Org. Synth., 2005, 82, 75.
• [11] H. Batra, R.M. Moriarty, R. Penmasta, V. Sharma, G. Stanciuc, J.P. Staszewski, S.M. Tuladhar, D.A. Walsh, Org. Process Res. Dev., 2006, 10, 484.
• [12] M.B. Fusaro, V. Chagnault, S. Josse, D. Postel, Tetrahedron, 2013, 69, 5880.
• [13] A. Fan, S. Jaenicke, G.-K. Chuah, Org. Biomol. Chem., 2011, 9, 7720.
• [14] I. Isaac, I. Stasik, D. Beaupere, R. Uzan, Tetrahedron Lett., 1995, 36, 383.
• [15] G.P. Silveira, C.B. Carvalho, T.S. Ribeiro, Preparaçao da d-ribonolactona empregando brometo e bromato de sódio. BR Patent 1020130323454, December 12, 2013.
• [16] H. Kold, I. Lundt,, Ch. Pedersen, Acta Chem. Skand., 1994, 48, 675.
• [17] H. Zinner, H. Voigt, J. Voigt, Carbohydr. Res., 1968, 7, 38.
• [18] N. Baggett, J.G. Buchanan, M.Y. Fatah, C.H. Lachut, K.J. McCullough J.M. Webber, J. Chem. Soc., Chem. Commun., 1985, 24, 1826.
• [19] S.-Y. Han, M.M. Joullié, Tetrahedron, 1993, 49, 349.
• [20] D.J. Lefeber, P. Steunenberg, J.F.G. Vliegenthart, J.P. Kamerling, Tetrahedron: Asymmetry, 2005, 16, 507.
• [21] L. Hough, J.K.N. Jones, D.L. Mitchell, Can. J. Chem. 1958, 36, 1720.
• [22] P. Nasomjai, D. O’Hagan, A.M.Z. Slawin, Beilstein J. Org. Chem., 2009, 5, No. 37, doi: 10.3762/bjoc.5.37.
• [23] M. Oba, S. Kawaji, H. Kushima, T. Sano, K. Nishiyama, J. Chem., 2013, Article ID 519415, doi:10.1155/2013/519415.
• [24] J. Lalot, G. Manier, I. Stasik, G. Demailly, D. Beaupére, Carbohydr. Res., 2001, 335, 55.
• [25] V. Bouchez, I. Stasik, D. Beaupere, R. Uzan, Tertrahedron Lett., 1997, 38, 7733.
• [26] C. Falentin, D. Beaupere, G. Demailly, I. Stasik, Carbohydr. Res., 2007, 342, 2807.
• [27] E. Burgos, A.K. Roos, S.L. Mowbray, L. Salmona, Tetrahedron Lett., 2005, 46, 3691.
• [28] R.E. Ireland, C.S. Wilcox, S. Thaisrivongs, J. Org. Chem., 1978, 43, 786.
• [29] R.E. Ireland, S. Thaisrivongs, N. Vanier, C.S. Wilcox, J. Org. Chem., 1980, 45, 48.
• [30] J.Ch.-Y. Cheng, U. Hacksell, G.D. Daves, Jr., J. Org. Chem., 1985, 50, 2778.
• [31] M. Okabe, R.-Ch. Sun, S.Y.-K. Tam, L.J. Todaro, D.L. Coffen, J. Org. Chem., 1988, 53, 4780.
• [32] C. Gonzalez, S. Kavoosi, A. Sanchez, S.F. Wnuk, Carbohydr. Res., 2016, 432, 17.
• [33] H.M. Cardozo, T.F. Ribeiro, M.M. Sá, D. Sebrao, M.G. Nascimento, G.P. Silveira, J. Braz. Chem. Soc., 2015, 26, 755.
• [34] M.M. Sá, G.P. Silveira, M.S. Castilho, F. Pavaob, G. Oliva, ARKIVOC 2002, (viii), 112.

Uwagi

Opracowanie rekordu w ramach umowy 509/P-DUN/2018 ze środków MNiSW przeznaczonych na działalność upowszechniającą naukę (2018).