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An Efficient Synthesis of 3′-Amino-3′-deoxyguanosine from Guanosine

✍ Scribed by Lei Zhang; Zhiyong Cui; Biliang Zhang

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
101 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

3′‐Amino‐3′‐deoxyguanosine was synthesized from guanosine in eight steps and 58% overall yield. The 2′,3′‐diol of 5′‐O‐[(tert‐butyl)diphenylsilyl]‐2‐N‐[(dimethylamino)methylidene]guanosine was reacted with α‐acetoxyisobutyryl bromide and treated with 0.5n NH~3~ in MeOH to yield 9‐{2′‐O‐acetyl‐3′‐bromo‐5′‐O‐[(tert‐butyl)diphenylsilyl]‐3′‐deoxy‐β‐D‐xylofuranosyl]‐2‐N‐[(dimethylamino)methylidene]guanine, which was reacted with benzyl isocyanate, NaH, and then 3.0n NaOH, and finally with Pd/C (10%) and HCO~2~NH~4~ in EtOH/AcOH to afford 3′‐amino‐3′‐deoxyguanosine.

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