Efficient synthesis of spacer-linked dimers of N-acetyllactosamine using microvawe-assisted pyridinium triflate-promoted glycosylations with oxazoline donors

Synlett

Volumn , Issue 9 SPEC. ISS., 2003, Pages 1255-1256

  Mohan, Halasayam ^a   Gemma, Emiliano ^a   Ruda, Katinka ^a   Oscarson, Stefan ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Glycoside; Glycosylations; Oligosaccharides

Indexed keywords

DIMER; GLYCOSIDE; LACTOSE; N ACETYLLACTOSAMINE; OXAZOLINE DERIVATIVE; PYRIDINIUM DERIVATIVE; PYRIDINIUM TRIFLATE; TOLUENESULFONIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CROSS LINKING; GLYCOSYLATION; HEATING; MICROWAVE RADIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0038780857     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40340     Document Type: Article

References (12)

1. Leffler, H. Trends Glycosci. Glycotechnol. 1997, 9, 9.
2. Perillo, N. L.; Marcus, M. E.; Baum, L. G. J. Mol. Med. 1998, 76, 402.
3. Danguy, A.; Camby, I.; Kiss, R. Biochim. Biophys. Acta 2002, 1572, 285.
4. Rabinovich, G. A.; Rubinstein, N.; Toscano, M. A. Biochim. Biophys. Acta 2002, 1572, 274.
5. Nangia-Makker, P.; Baccarini, S.; Raz, A. Curr. Top. Biochem. Res. 2000, 3, 229.
6. Brewer, F. Biochim. Biophys. Acta 2002, 1572, 255.
7. Banoub, J.; Boullanger, P.; Lafont, D. Chem. Rev. 1992, 92, 1167.
8. Yohino, T.; Sato, K.-I.; Wanme, F.; Takai, I.; Ishido, Y. Glycoconj. J. 1992, 9, 287.
9. Wittman, W.; Lennartz, D. Eur. J. Org. Chem. 2002, 1363.
10. 13C NMR and MALDI-TOF MS.
11. Söderberg, E.; Westman, J.; Oscarson, S. J. Carbohydr. Chem. 2001, 20, 397.
12. 2 (1 mL) and heated in a sealed vessel in a Smithsynthesizer, a single mode microwave cavity from Personal Chemistry, with a set cut-off temperature of 80°C for 20 min. Purification directly on a silica gel column (EtOAc/MeOH) gave products 7-10 (62-71%).