|
KMID : 0043319990220060619
|
|
Archives of Pharmacal Research
1999 Volume.22 No. 6 p.619 ~ p.623
|
|
|
Synthesis of 2’,3’-Dideoxyisoguanosine from Guanosine
|
|
Kim Sung-Han
Lee Sang-Jun
Sun Won-Suck
Oh Sung-Wook
Kim Jung-Han
|
|
|
Abstract
|
|
|
|
-dideoxyisoguanosine was synthesized from guanosine via intermediate 6-[(4-methyl-phenyl)thio]-2-oxo-9-(-tri-O-acetyl--D-ribofuranosyl)-2,3-dihydropurine (4). The 2-oxo, 6-amino and -hydroxy triprotected isoguanosine derivative was utilized to reduce high polarity and promote poor solubility of intermediates. The protecting groups for oxo and 6-amino were easily removed in reduction of olefin in ribose without additional reaction steps.-Vicinal diol in ribose sugar moiety was transformed to olefin with Bu3SnH by radical reaction via bisxanthate. Removing -O-TBDMS protecting group gave final product, -dideoxyisoguanosine (12) in a 10% overall yield.
|
|
|
KEYWORD
|
|
|
2’, 3’-Dideoxyisoguanosine, Guanosine, Isoquanosine, Antiviral agent
|
|
|
FullTexts / Linksout information
|
|
|
|
|
|
Listed journal information
|
|
  
|