Use of controlled pore glass in solid phase oligosaccharide synthesis. Application to the semiautomated synthesis of a glyconucleotide conjugate

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 1953-1956

  Adinolfi, Matteo ^a   Barone, Gaspare ^a   De Napoli, Lorenzo ^a   Iadonisi, Alfonso ^a   Piccialli, Gennaro ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

GLASS; GLYCOCONJUGATE; NUCLEOTIDE DERIVATIVE; OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; GLYCOSYLATION; REACTION ANALYSIS; SOLID STATE;

EID: 0032473849     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00103-8     Document Type: Article

References (25)

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11. 6. Gait; M. J. Oligonucleotide synthesis: a practical approach, IRL Press: Oxford, 1984.
12. 7. During the preparation of this manuscript, R. R. Schmidt touched on some results concerning the use of CPG in solid-phase glycosylations at the 9th European Carbohydrate Symposium, 1997, Utrecht (Netherlands), Abstract Book, p. 59.
13. 8. Prepared from commercially available 4,6-O-benzylidene-α-methyl-D-glucopyranoside through acetylation of 2-OH and 3-OH, removal of the benzylidene protecting group, regioselective dimethoxytritylation of 6-OH and succinylation of 4-OH (65 % overall yield).
14. 9. Amino group loading of the supports: TG 0.22 mmol/g, PS (1% DVB) 1.18 mmol/g, CPG 30-35 μmol/g.
15. 10. Obtained functionalizations: 0.14-0.18 mmol/g for 5, 0.22-0.24 mmol/g for 6, 25-30 μmol/g for 7.
16. 1,2= 8.1 Hz, β-Glcp H-1); methoxyl protons at δ 3.39 (3H, s); AcO protons at δ 2.10, 2.07, 2.05, 2.03, 2.02, 2.01, 2.00 (singlets).
17. 12 De Napoli, L.; Messere, A., Montesarchio, D.; Pepe, A.; Piccialli, G.; Varra, M. J. Org. Chem. 1997, in press; De Napoli, L.; Di Fabio, G.; Messere, A.; Pepe A., Varra, M.; Piccialli, G. Gazz. Chim. It. 1996, 112, 755-759. De Napoli, L.; Galeone, G.; Mayol, L.; Messere, A.; Montesarchio, D.; Piccialli, G. Bioorg. Med. Chem. 1995, 3, 1325-1329.
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21. Roth, R.; Kliem, H-C.; Wiessler, M. 9th European Carbohydrate Symposium, 1997, Utrecht (Netherlands), Abstract Book, p. 229.
22. 14. Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 543-584.
23. 15 The incorporation of the nucleotide was performed on a Millipore Cyclone Plus automated synthesizer.
24. 3CN in 0.1 M triethylammonium acetate, pH 7; flow 0.6 mL/min; retention time of 13: 9.1 min.
25. -.