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6-isobutyrylaminopurine: A convenient building block for the synthesis of carbocyclic adenosine analogs

✍ Scribed by Jinglan Zhou; Kamal Bouhadir; Thomas R. Webb; Philip B. Shevlin


Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
155 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis


Readily available 6-isobutyrylaminopurine can replace either a primary or secondary OH group under Mitsunobu conditions and provide an effkient synthesis of carbocyclic analogs of adenosine. X-my data indicates that only tbe desired @-substituted derivatives of adenine are formed.


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## Abstract (+)‐(1__R__,4__R__)‐Bicyclo[2.2.1]hept‐5‐en‐2‐one (7) was prepared in 78.5% yield by oxidative degradation of (+)‐(1__R__)‐__endo__‐bicyclo[2.2.1]hept‐5‐ene‐2‐carboxylic acid (4) by using an improved procedure for the oxidation of the dianion of 4 with dioxygen. Dihydroxylation of 7 wit