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Efficient synthesis of protected 3′-deoxyadenosine and 3′-deoxyguanosine from adenosine and guanosine

✍ Scribed by Zhiyong Cui; Lei Zhang; Biliang Zhang


Book ID
104211585
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
74 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis


Highly efficient synthesis of protected 3%-deoxyadenosine and 3%-deoxyguanosine from adenosine and guanosine were described. The 2%,3%-diol of protected adenosine and guanosine were reacted with a-acetoxyisobutyryl bromide to yield 9-(2%-Oacetyl-3%-bromo-5%-O-tert-butyldiphenylsilyl-3%-deoxy-b-D-xylofuranosyl)-6-N-benzoyl adenine and 9-(2%-O-acetyl-3%-bromo-5%-Otert-butyldiphenylsilyl-3%-deoxy-b-D-xylofuranosyl)-2-N-(N%,N%-dimethylaminomethylene) guanine and subsequently heated with tri-n-butyltin hydride in the presence of 2,2%-azobisisobutyronitrile to afford the protected 3%-deoxyadenosine and 3%deoxyguanosine in 66-73% over all yield.


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