PREPARATION AND PROPERTIES OF O'-METHYL DERIVATIVES OF 9-BETA-D-ARABINOFURANOSYLADENINE

  • 1 January 1976
    • journal article
    • research article
    • Vol. 1  (4) , 203-209
Abstract
The previously reported resistance of 9-substituted adenines to ring alkylation in alkaline medium was profited from to prepare all 7 possible O''methyl derivatives of the [cancer] therapeutically important 9-.beta.-D-arabinofuranosyladenine (araA) by mild methylation of the latter with dimethylsulfate in aqueous alkaline medium. All products were fractionated and isolated in a single step on a Dowex OH- column. The sequence of elution of the various derivatives was strikingly similar to that for the O''methyl derivatives of 1-.beta.-D-arabinofuranosylcytosine, previously reported, suggestive of a similar sequence of acidities of the sugar hydroxyls. The products were identified by various criteria, including PMR spectroscopy, extensive data for which are supplied. The 2''-O-methyl and 3''-O-methyl derivatives of araA exhibited appreciably lower susceptibility to calf intestinal adenosine deaminase than the parent araA. The 5''-O-methyl analogue was fully resistant to enzymatic deamination.

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