Ribonucleoside-derivative and method for preparing the same

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 253, 536 2534, 536 267, 536 2674, 536 268, 536 269, C07H 2102

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059860847

ABSTRACT:
The ribonucleoside-derivatives serve for the synthesis of ribonucleic acids and comprise a triple substituted silyloxymethyl-group as a protection-group on the oxygen atom in 2'-position. The ribonucleoside-derivatives may be suitably protected on the nucleo-base and on the oxygen in 5'-position also. The new protection-groups in 2'-O-position are superior to conventional such protection-groups as they are not subject to isomerization and give higher coupling yields. The general formula of the ribonucleoside-derivative is: ##STR1## whereby R.sup.1 is a base of the purine- or pyrimidine-family or a derivative of such a base,

REFERENCES:
MacLeod et al., "Mass Spectroscopy of Cytokinin Metabolites. Per(trimethylsilyl) and Permethyl Derivatives of Glucosides of Zeatin and 6-Benzylaminopurine," J. Organic Chemistry, 41(25), 3959-3967 (Dec. 10, 1976).
Nagatsugi et al., "2-Aminopurine Derivatives with C6-Substituted Olefin as Novel Cross-Linking Agents and the Synthesis of the Corresponding .beta.-Phosphoramidite Precursors," Tetrahedron, 53(9), 3035-3044 (Mar. 3, 1997).
Boons et al., "Use of (Phenyldimethylsilyl)methoxxymethyl and (Phenyldimethylsilyl)methyl Ethers as Protecting Groups for Sugar Hydroxyls," Tetrahedron Letters, 31(15), 2197-2200 (1990).
Usman et al. "Automated Chemical Synthesis of Long Oligoribonucleotides Using 2'-O-Silylated Ribonucleoside 3'-O-Phosphoramidites on a Controlled-Pore Glass Support: Synthesis of a 43-Nucleotide Sequence Similar to the 3'-Half Molecule of an Escherichia coli Formylmethionine tRNA" Journal of the American Chemical Society, vol. 109, pp. 7845-7854, (Sep. 12, 1987).

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