Psoralen-nucleoside adducts and method for their preparation

Details Psoralen-nucleoside adducts and method for their preparation Psoralen-nucleoside adducts and method for their preparation

1987-06-16

1989-05-02

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 22, 549282, C07H 19067, C07H 19073, C07H 1904, C07D49300

Patent

active

048269670

ABSTRACT:
A method for the stereoselective snythesis of a cis-syn, furan-side mono-adducted linear furocoumarin:nucleoside adduct, which comprises reacting a linear furocoumarin with a nucleophilic acid to form a 3,4-dihydro-4-substituted linear furocoumarin intermediate, and contacting the intermediate with a nucleoside under photoactivating conditions. The reaction produces a cis-syn, furan-side, mono-adducted 3,4-dihydro-4-substituted linear furocoumarin:nucleoside adduct which can then be deblocked to give the final product under mild conditions.

REFERENCES:
patent: 4599303 (1986-07-01), Yabusahi et al.
Asker et al., the Chemical Abstracts; col. 520b, vol. 54, 1960.
Shim et al., the Chemical Abstracts, 99:154432y (1983).
Vigny et al., the Chemical Abstracts, 99:206149h (1983).
Cadet et al., the Chemical Abstracts, 106; 152168f (1987).
Jones et al., Nouv. J. Chem. (1985) 9:5-6.
Binkley et al., "Synthetic Organic Photochemistry," W. M. Horspool Ed. Plenum: New York, 1984.

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