Propargyl modified nucleosides and nucleotides

Details Propargyl modified nucleosides and nucleotides Propargyl modified nucleosides and nucleotides

1995-07-25

1998-04-28

Kight, Joe

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

Organic compounds

Carbohydrates or derivatives

536 2534, 536 2626, 536 266, 536 267, 536 2671, 536 276, 536 2781, 536 285, 536 2853, 536 231, 536 243, 536 245, C07H 1967, C07H 1910, C07H 19167, C07H 1920

Patent

active

057445958

ABSTRACT:
The present invention describes a novel 2'-O-alkylation reaction to produce a novel series of nucleosides carrying the 2'-O-propargyl group, using propargyl bromide, dibutyl tin oxide and tetrabutyl ammonium bromide. The procedure involves novel techniques for regioselective introduction of 2'-/3'-O-propargyl group directly on the 5'-DMT-N-protected- nucleosides using dibutyl tin oxide as a mild base in conjunction with a phase transfer catalyst, tetrabutyl ammonium bromide. The reaction process has many significant features and leads to isomeric ratios in favor of the 2'-regio isomer. This allows the synthesis of the corresponding phosphoramidites of high purity.

REFERENCES:
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