| 摘要 |
<p>PURPOSE: To obtain the subject derivative such as azidothymidine(AZT) in high yield, selectivity and purity by respectively protecting hydroxyl groups at the 5'- and the 3'-positions of a 2'-deoxyuridine derivative with an aromatic acyl group and sulfonyl group, anhydrizing the resultant derivative at the 2,3'- positions and then converting the prepared compound into an azide. CONSTITUTION: The hydroxyl group at the 5'-position of a 2'-deoxyuridine derivative of formula I [X is H, a halogen, a (substituted)alkyl, a (substituted) aryl, etc.] is esterified with an aromatic acyl group and protected and the hydroxyl group at the 3'-position is then sulfonic esterified with an alkylsulfonyl group, protected and then anhydrized at 2,3'-positions with a strong base such as 1,8-diazabicyclo[5.4.0]undec-7-ene to provide a 2,3'-anhydrized derivative of formula II (R<3> is a protecting group of hydroxyl group). The resultant derivative is subsequently reacted with sodium azide in the presence of an ammonium salt to afford the objective nucleoside derivative azide of formula III represented by the AZT in high yield, selectivity and purity.</p> |
