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Volumn 72, Issue 1, 2007, Pages 173-179

High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSYLATION; NUCLEOSIDES; REGIOISOMERS; RIBOSYLATION;

EID: 33846067733     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061885l     Document Type: Article
Times cited : (54)

References (64)
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    • The pioneering work of Emil Fischer in the fields of purines, carbohydrates, and proteins set the foundation for later advances in the field of nucleosides. (a) Fischer, E
    • The pioneering work of Emil Fischer in the fields of purines, carbohydrates, and proteins set the foundation for later advances in the field of nucleosides. (a) Fischer, E. Chem. Ber. 1897, 30, 1846-1859.
    • (1897) Chem. Ber , vol.30 , pp. 1846-1859
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    • (b) Fischer, E. Chem. Ber. 1898, 31, 104-122.
    • (1898) Chem. Ber , vol.31 , pp. 104-122
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    • (c) Fischer, E. Chem. Ber. 1899, 32, 267-273.
    • (1899) Chem. Ber , vol.32 , pp. 267-273
    • Fischer, E.1
  • 4
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    • The term nucleoside was introduced in 1909 by Levene and Jacobs. Levene, P. A.; Jacobs, W. A. Chem. Ber. 1909, 42, 2474-2478.
    • The term nucleoside was introduced in 1909 by Levene and Jacobs. Levene, P. A.; Jacobs, W. A. Chem. Ber. 1909, 42, 2474-2478.
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    • Amine substitution of nucleoside heteroaryl-halides: (a) Rodenko, B; Wanner, M. J.; Koomen, G.-J. J. Chem. Soc., Perkin Trans. 1 2002, 1247-1252.
    • Amine substitution of nucleoside heteroaryl-halides: (a) Rodenko, B; Wanner, M. J.; Koomen, G.-J. J. Chem. Soc., Perkin Trans. 1 2002, 1247-1252.
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    • Palladium-coupling mediated derivatization: Aucagne, V.; Berteina-Raboin, S.; Guenot, P.; Agrofoglio, L. A. J. Comb. Chem. 2004, 6, 717-723.
  • 21
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    • Formation of amides, ureas, and carbamates on the ribose moiety: (a) Golisade, A.; Bressi, J. C.; Van Calenbergh, S.; Gelb, M. H.; Link, A. J. Comb. Chem. 2000, 2, 537-544.
    • Formation of amides, ureas, and carbamates on the ribose moiety: (a) Golisade, A.; Bressi, J. C.; Van Calenbergh, S.; Gelb, M. H.; Link, A. J. Comb. Chem. 2000, 2, 537-544.
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    • Direct evaporation of the reaction mixture prior to chromatographic purification decomposed some reaction products, resulting in decreased yields
    • Direct evaporation of the reaction mixture prior to chromatographic purification decomposed some reaction products, resulting in decreased yields.
  • 40
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    • The automated silica gel MPLC process purified most glycosylation products to homogeneity. However, a few contained impurities related to excess sugar byproducts or excess base. These were conveniently removed with automated silica gel MPLC or precipitation of the nucleoside product after the deacylation reaction so that the final nucleoside product could be obtained in high purity
    • The automated silica gel MPLC process purified most glycosylation products to homogeneity. However, a few contained impurities related to excess sugar byproducts or excess base. These were conveniently removed with automated silica gel MPLC or precipitation of the nucleoside product after the deacylation reaction so that the final nucleoside product could be obtained in high purity.
  • 42
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    • A silica supported fusion glycosylation in a standard kitchen microwave is the only report of a microwave assisted glycosylation: Andrzejewska, M.; Kaminski, J.; Kazimierczuk, Z. Nucleosides, Nucleotides, Nucleic Acids 2002, 21, 73-78.
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    • 6) with reported values: (a) Ishido, Y.; Nakazaki, N.; Sakairi, N. J. Chem. Soc., Perkin Trans. 1 1979, 2088-2098.
    • 6) with reported values: (a) Ishido, Y.; Nakazaki, N.; Sakairi, N. J. Chem. Soc., Perkin Trans. 1 1979, 2088-2098.
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    • Other reports have documented the selective deprotection of tri- and tetra-benzoyl-protected nucleosides to yield 5′-O-benzoyl- protected nucleosides using hydrazine hydrate, ammonia, sodium methoxide, or lithium 2,2,2-trifluoroethoxide as the deacylating reagent. See ref 25a and (a) Ferris, J. P, Devadas, B, Huang, C.-H, Ren, W.-Y. J. Org. Chem. 1985, 50, 747-754
    • Other reports have documented the selective deprotection of tri- and tetra-benzoyl-protected nucleosides to yield 5′-O-benzoyl- protected nucleosides using hydrazine hydrate, ammonia, sodium methoxide, or lithium 2,2,2-trifluoroethoxide as the deacylating reagent. See ref 25a and (a) Ferris, J. P.; Devadas, B.; Huang, C.-H.; Ren, W.-Y. J. Org. Chem. 1985, 50, 747-754.
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    • This process, known as Nucapalooza in our labs, has been applied successfully to the production of more than 400 nucleosides from the reaction of six different acylated ribofuranosyl derivatives with a set of bases which included those listed in Table 1 and the Supporting Information Table S1
    • This process, known as Nucapalooza in our labs, has been applied successfully to the production of more than 400 nucleosides from the reaction of six different acylated ribofuranosyl derivatives with a set of bases which included those listed in Table 1 and the Supporting Information Table S1.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.