Adenine 9-glucosyl

Silyl derivatives of purines are commonly used in the same way as in a synthesis of 9-(a, -D-glucopyranosyl)adenine from AT -benzoyl-9-bis(trimethylsilyl)adenine and 2,3,4,6-tetra-O-acetyl-a-D-glucosyl chloride at 150-160 °C over 4 hours to produce, after deblocking, a mixture of anomeric nucleosides (B-68MI40901,p. 135). The hypoxanthine nucleosides may be obtained in a similar fashion or by deamination of the adenine derivatives. 

The reaction of 3,4,6-tri-0-acetyl-2-deoxy-2-phthalimido-D-glucopy-ranosyl chloride with the chloromercuri derivative of Ar ,iV -dimethyl-2-(methylthio)adenine, followed by desulfurization and de-O-acylation gave 9-(2-acetamido-2-deoxy-/3-D-glucosyl)-iV ,i -dimethyladenine (69)This... 

It is quite often most convenient to prepare a desired purine nucleoside by transformations at the purine moiety of another purine nucleoside. Perhaps the most useful and frequently employed transformation is the nucleophilic displacement of a chlorine atom or an alkylthio group attached to C-2, C-6, or C-8 of the purine nucleus. In his early work, Fischer established that the order of reactivity of the chlorine atoms attached to a purine is Cl-6 > Cl-2 Cl-8, so that, by choosing the proper sequence of reactions, a variety of products can be obtained. Thus, as already described, Fischer was able to prepare the n-glucosyl analogs of adenine and guanosine by the appropriate transformations of 2,8-dichloro-9- -D-glucopyranosyladenine. 

Isopentenyl adenosine Molecular weight Isopentenyl adenine Diphenylurea O-glucosyl zeatin Dihydrozeatin Zeatin... 

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