Process for the preparation of 2'-O-alkyl purine phosphoramidite

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

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536 267, 536 2671, 536 2672, 536 2721, 536 2781, C07H 1920

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056462654

ABSTRACT:
2'-O-alkylated guanosine, uridine, cytidine, and 2,6-diaminopurine 3'-O-phosphoramidites are prepared by alkylating nucleoside precursors, adding suitable blocking groups and phosphitylating. Alkylation is effected on 2,6-diamino-9-(.beta.-D-ribofuranosyl)purine followed by deamination to prepare guanosine 2'-O-alkylated 3'-O-phosphormidites. Alkylation is effected on a dialkyl stannylene derivative of uridine to prepare uridine 2'-O-alkylated 3'-O-phosphormidites. Alkylation is effected directly on cytidine to prepare cytidine 2'-O-alkylated 3'-O-phosphormidites. Alkylation is effected directly on 2,6-diaminopurine to prepare 2,6-diaminopurine 2'-O-alkylated 3'-O-phosphormidites.

REFERENCES:
patent: 4725677 (1988-02-01), Koster et al.
patent: 5214135 (1993-05-01), Srivastava et al.
patent: 5466786 (1995-11-01), Buhr et al.
Khurshid et al., FEBS Letters 1972, 28:1, 25.
Kielanowska et al., Nucleic Acids Research 1976, 3:3,817.
Kusmierek et al., ACTA Biochimica Polonica 1973, 20:4,365.
Pike et al., J. Org. Chem. 1974, 39:25,3674.
Ransford et al., J. Carbohydrates--Nucleosides--Nucleotides 1974, 1:3,275.
Rottman et al., Biochemistry 1974, 13,2762.
Tazawa et al., Biochemistry 1972, 11,4931.
Berner et al., "Studies on the role of tetrazole in the activation of phosphoramidites", Nucleic Acids Research 1989, 17, 853-864.
Cotten, et al., "2'-O-methyl, 2'-O-ethyl oligoribonucleotides and phosphorothioate oligodeoxyribonucleotides as inhibitors of the in vitro U7 snRNP-dependent mRNA processing event", Nucleic Acids Research, 1991, 19, 2629-2635.
Dahl et al., "Mechanistic studies on the phosphoramidite coupling reaction in oligonucleotide synthesis. I. Evidence for nucleophilic catalysis by tetrazole and rate variations with the phosphorus substituents", Nucleic Acids Research 1987, 15, 1729-1743.
Inoue, et al., "Synthesis and hybridization studies on two complementary nona(2'-O-methyl)ribonucleotides", Nucleic Acids Research, 1987, 15, 6131-6148.
Nielsen et al. "Thermal Instability of Some Alkyl Phosphorodiamidites", J. Chem. Research 1986, 26-27.
Robins, et al., "Nucleic Acid Related Compounds. 12. The Facile and High-Yield Stannous Chloride Catalyzed Monomethylation of the Cis-Glycol System of Nucleosides by Diazomethane", J. Org. Chem., 1974, 39, 1891-1899.
Robins, "Nucleic acid related compounds. 36. Synthesis of the 2'-O-methyl and 3'-O-methyl ethers of guanosine and 2-aminoadenosine and correlation of O'-methylnucleoside .sup.13 C nmr spectral shifts", Can. J. Chem. 1981, 59, 3360-3364.
Singer, et al., "Alkylation of Ribose in RNA Reacted with Ethylnitrosourea at Neutrality", Biochemistry 1976, 15, 5052-5057.
Sproat, et al, "New synthetic routes to protected purine 2'-O-methylriboside-3'-O-phosphoramidites using a novel alkylation procedure", Nucleic Acids Research, 1990, 18, 41-49.
Sproat et al., "2'-O-Methyloligoribonucleotides: synthesis and applications", Oligonucleotides and Analogs A Practical Approach; Eckstein, F. Ed.; IRL Press, Oxford, 1991, 49-86.
Sproat, et. al., "New synthetic routes to synthons suitable for 2'-O-allyloligoribonucleotide assembly", Nucleic Acids Research, 1991 19, 733-738.
Wagner, et al., "A simple procedure for the preparation of protected 2'-O-methyl or 2'-O-ethyl ribonucleoside-3'-O-phosphoramidites", Nucleic Acids Research, 1991, 19, 5965-5971.
Wagner et al., "Preparation and Synthetic Utility of Some Organotin Derivatives of Nucleosides", J. Org. Chem. 1974, 39, 24-30.
Iribarren et al., "2'-O-Alkyl Oligoribonucleotides as Antisense Probes", Proc. Natl. Acad. Sci. USA 87: 7747-7751 (1990).
Chavis, C. et al., "Synthesis of 2',3'-Differentiated Ribonucleosides via Lycosylation Reactions with 2'-O-TBDMS Ribofuranose Derivatives. A. Pyrimidine Series", J. Org. Chem. 1982, 47, 202-206.
Divakar, K.J. et al., "Reaction Between 2,2'-Anhydro-1-.beta.-p-arabinofuranosyluracil and Thiolate Ions", J. Chem. Soc. Perkin Trans. 1982, 1625-1628.

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