Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1993-03-29
1995-07-25
Robinson, Douglas W.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 253, C07H 19067, C07H 19167
Patent
active
054363314
ABSTRACT:
A process for protecting the 2'-hydroxyl of a nucleoside, which can then be used in the chemical synthesis of polyribonucleotides, comprising the reacting of a protected nucleoside of formula I ##STR1## wherein B is a nucleoside heterocyclic base and R' is a hydroxyl-protecting group,
with 1-N-aryl-4-alkoxy-1,2,5,6-tetrahydropiperidine of formula II ##STR2## wherein Ar is an aryl group possessing an electron-withdrawing substituent which renders said protecting group acid labile and R is C.sub.1 -C.sub.4 alkyl,
in the presence of an acid catalyst and a solvent to yield the compound of formula II below: ##STR3##
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Taylor et al. Synthesis, pp. 606-608, 1981.
Gallagher et al. J. Chem. Soc. pp. 5110-5120, 1962.
Reese et al. Tetrahedron Letters 27:2291-2244, 1986.
Narang et al. Total Synth. Nat. Prod. 6:51-84, 1984.
Casy, Chem. Abstr. No. 61:8267c, Sep., 1964, Experientia, 20(8):437-438, 1964.
Brookes et al, Chem. Abstr. No. 51:17909a, Nov., 1957, J. Chem. Soc., pp. 3173-3175, 1957.
Reese et al. Tetrahedron Lett. 25, 3015, 1984.
King's College London
Kunz Gary L.
Robinson Douglas W.
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