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An Efficient Synthesis of 3′‐Amino‐3′‐deoxyguanosine from Guanosine
Author(s) -
Zhang Lei,
Cui Zhiyong,
Zhang Biliang
Publication year - 2003
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200390069
Subject(s) - chemistry , guanosine , deoxyguanosine , yield (engineering) , bromide , guanine , medicinal chemistry , isocyanate , stereochemistry , organic chemistry , nucleotide , adduct , biochemistry , materials science , polyurethane , gene , metallurgy
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 0.5 n 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 3.0 n NaOH, and finally with Pd/C (10%) and HCO 2 NH 4 in EtOH/AcOH to afford 3′‐amino‐3′‐deoxyguanosine.