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Abstract:

A new and efficient three-step procedure for the synthesis of 1,6-anhydro-α-D-galactofuranose is described. The key step involves the formation of the galactofuranosyl iodide by treatment of per-O-TBS-D-Galf with TMSI, the selective 6-O-desilylation by an excess of TMSI, and the simultaneous nucleophilic attack of the 6-hydroxy group on the anomeric carbon, with the iodide as a good leaving group. This compound is a good precursor for building blocks for the construction of 1→6 linkages. © 2014 Baldoni and Marino.

Registro:

Documento: Artículo
Título:Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools
Autor:Baldoni, L.; Marino, C.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Palabras clave:1,6-anhydro-α-D-Galf; Galactofuranosyl iodide; Galactofuranosyl precursor; Per-tert-butyldimethylsilyl-β-D-galactofuranose
Año:2014
Volumen:10
Página de inicio:1651
Página de fin:1656
DOI: http://dx.doi.org/10.3762/bjoc.10.172
Título revista:Beilstein Journal of Organic Chemistry
Título revista abreviado:Beilstein J. Org. Chem.
ISSN:18605397
CODEN:BJOCB
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_18605397_v10_n_p1651_Baldoni

Referencias:

  • Cerny, M., Chemistry of anhydro sugars (2003) Advances in Carbohydrate Chemistry and Biochemistry, 58, pp. 121-198. , DOI 10.1016/S0065-2318(03)58004-0
  • Bols, M., (1996) Carbohydrate Building Blocks, , Wiley: Chichester
  • Kulkarni, S.S., Lee, J.-C., Hung, S.-C., Recent advances in the applications of D- and L-form 1,6- anhydrohexopyranoses for the synthesis of oligosaccharides and nature products (2004) Current Organic Chemistry, 8 (6), pp. 475-509. , DOI 10.2174/1385272043485800
  • Lafont, D., Boullanger, P., Cadas, O., Descotes, G., (1989) Synthesis, pp. 191-194. , doi:10.1055/s-1989-27192
  • Boons, G.-J., Isles, S., Setälä, P., (1995) Synlett, pp. 755-756. , doi:10.1055/s-1995-5057
  • Skorupowa, E., Dmochowska, B., Madaj, J., Kasprzykowski, F., Sokolowski, J., Wiśniewski, A., (1998) J. Carbohydr. Chem., 17, pp. 49-59. , doi:10.1080/07328309808005768
  • Lauer, G., Oberdofer, F., (1993) Angew. Chem., Int. Ed. Engl., 32, pp. 272-273. , doi:10.1002/anie.199302721
  • Nicolaou, K.C., Seitz, S.P., Papahatjis, D.P., (1983) J. Am. Chem. Soc., 105, pp. 2430-2434. , doi:10.1021/ja00346a053
  • Xue, J., Guo, Z., A facile synthesis of Cerny epoxides and selectively blocked derivatives of 2-azido-2-deoxy-β-D-glucopyranose (2001) Tetrahedron Letters, 42 (37), pp. 6487-6489. , DOI 10.1016/S0040-4039(01)01354-5, PII S0040403901013545
  • Chun, Y., Yan, S., Li, X., Ding, N., Zhang, W., Wang, P., Li, M., Li, Y., (2011) Tetrahedron Lett., 52, pp. 6196-9198. , doi:10.1016/j.tetlet.2011.09.055 And references therein
  • Alexander, B.H., Dimler, R.J., Mehltretter, C.L., (1951) J. Am. Chem. Soc., 73, pp. 4658-4659. , doi:10.1021/ja01154a048
  • Hann, R.M., Hudson, C.S., (1941) J. Am. Chem. Soc., 63, pp. 2241-2242. , doi:10.1021/ja01853a061
  • Richtmyer, B.H., (1963) Methods Carbohydr. Chem., 2, pp. 390-394
  • Hoai, N.T., Sasaki, A., Sasaki, M., Kaga, H., Kakuchi, T., Satoh, T., (2011) Biomacromolecules, 12, pp. 1891-1899. , doi:10.1021/bm2002413
  • Lin, J.W.-P., Schuerch, C., (1972) Macromolecules, 5, pp. 656-657. , doi:10.1021/ma60029a026
  • Sakar, S.K., Choudhury, A.K., Mukhopadhyay, B., Roy, N., (1999) J. Carbohydr. Chem., 18, pp. 1121-1130. , doi:10.1080/07328309908544059
  • Sakar, S.K., Choudhury, A.K., Hirsch, J., Roy, N., Synthesis of 1,6-anhydro-2,3,5-tri-O-benzoyl-α-D-galactofuranose (2011) Carbohydrate Chemistry. Proven Synthetic Methods, 1, pp. 269-278. , Kováč, P., Ed.; CRC Press: Boca Raton, USA
  • De Lederkremer, R.M., Colli, W., (1995) Glycobiology, 5, pp. 547-552. , doi:10.1093/glycob/5.6.547
  • Pedersen, L.L., Turco, S.J., Galactofuranose metabolism: A potential target for antimicrobial chemotherapy (2003) Cellular and Molecular Life Sciences, 60 (2), pp. 259-266. , DOI 10.1007/s000180300021
  • Marino, C., De Lederkremer, R.M., Galactose configurations in nature with emphasis on the biosynthesis of galactofuranose in glycans (2014) Galactose: Structure and Function in Biology and Medicine, pp. 107-134. , Pomin, V. H., Ed.; Nova Publisher: New York, USA
  • Peltier, P., Euzen, R., Daniellou, R., Nugier-Chauvin, C., Ferrières, V., (2008) Carbohydr. Res., 343, pp. 1897-1923. , doi:10.1016/j.carres.2008.02.010
  • Richards, M.R., Lowary, T.L., (2009) Chem Bio Chem, 10, pp. 1920-1938. , doi:10.1002/cbic.200900208
  • Akihiro, I., Lowary, T., (2011) Trends Glycosci. Glycotechnol., 23, pp. 134-152. , doi:10.4052/tigg.23.134
  • Marino, C., Baldoni, L., (2014) Chem Bio Chem, 15, pp. 188-204. , doi:10.1002/cbic.201300638
  • Marino, C., Gallo-Rodriguez, C., De Lederkremer, R.M., Galactofuranosyl containing glycans: Occurrence, synthesis and biochemistry (2012) Glycans: Biochemistry, Characterization and Applications, pp. 207-268. , Mora-Montes, H. M., Ed.; Nova Science Publisher: Boca Raton, USA
  • Crick, D.C., Mahaprata, S., Brennan, P.J., (2001) Glycobiology, 11, pp. 107R-118R. , doi:10.1093/glycob/11.9.107R
  • Besra, G.S., Khoo, K.-H., McNeil, M.R., Dell, A., Morris, H.R., Brennan, P.J., (1995) Biochemistry, 34, pp. 4257-4266. , doi:10.1021/bi00013a015
  • Bhamidi, S., Scherman, M.S., Rithner, C.D., Prenni, J.E., Chatterjee, D., Koo, K.-H., McNeil, M.R., (2008) J. Biol. Chem., 283, pp. 12992-13000. , doi:10.1074/jbc.M800222200
  • Zhang, G., Fu, M., Ning, J., An efficient and concise synthesis of a β-(1→6)-linked d-galactofuranosyl hexasaccharide (2005) Carbohydrate Research, 340 (1), pp. 155-159. , DOI 10.1016/j.carres.2004.11.001, PII S0008621504004598
  • Splain, R.A., Kiessling, L.L., (2010) Bioorg. Med. Chem., 18, pp. 3753-3759. , doi:10.1016/j.bmc.2010.04.068
  • Levengood, M.R., Splain, R.A., Kiessling, L.L., (2011) J. Am. Chem. Soc., 133, pp. 12758-12766. , doi:10.1021/ja204448t
  • Baldoni, L., Marino, C., (2009) J. Org. Chem., 74, pp. 1994-2003. , doi:10.1021/jo8025274
  • Baldoni, L., Stortz, C.A., Marino, C., (2011) Carbohydr. Res., 346, pp. 191-196. , doi:10.1016/j.carres.2010.11.013
  • Baldoni, L., Marino, C., (2012) Carbohydr. Res., 362, pp. 70-78. , doi:10.1016/j.carres.2012.08.021
  • Baldoni, L., Marino, C., (2013) Carbohydr. Res., 374, pp. 75-81. , doi:10.1016/j.carres.2013.03.032
  • Corey, E.J., Venkateswarlu, A., (1972) J. Am. Chem. Soc., 94, pp. 6190-6191. , doi:10.1021/ja00772a043
  • Köll, P., Angyal, S.J., (1988) Carbohydr. Res., 179, pp. 1-5. , doi:10.1016/0008-6215(88)84104-1
  • Marino, K., Marino, C., De Lederkremer, R.M., Specific tritium labeling of β-D-galactofuranosides at the 6-position: A tool for β-D-galactofuranosidase detection (2002) Analytical Biochemistry, 301 (2), pp. 325-328. , DOI 10.1006/abio.2001.5508
  • Sauvageau, J., Foster, A.J., Khan, A.A., Chee, S.H., Sims, I.M., Timmer, M.S.M., Stocker, B.L., (2012) Chem Bio Chem, 13, pp. 2416-2424. , doi:10.1002/cbic.201200468

Citas:

---------- APA ----------
Baldoni, L. & Marino, C. (2014) . Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools. Beilstein Journal of Organic Chemistry, 10, 1651-1656.
http://dx.doi.org/10.3762/bjoc.10.172
---------- CHICAGO ----------
Baldoni, L., Marino, C. "Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools" . Beilstein Journal of Organic Chemistry 10 (2014) : 1651-1656.
http://dx.doi.org/10.3762/bjoc.10.172
---------- MLA ----------
Baldoni, L., Marino, C. "Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools" . Beilstein Journal of Organic Chemistry, vol. 10, 2014, pp. 1651-1656.
http://dx.doi.org/10.3762/bjoc.10.172
---------- VANCOUVER ----------
Baldoni, L., Marino, C. Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools. Beilstein J. Org. Chem. 2014;10:1651-1656.
http://dx.doi.org/10.3762/bjoc.10.172