Conversion of guanosine into acyclovir and its 6-deoxy derivative

Add time:08/18/2019    Source:sciencedirect.com

2-Amino-6-(4-chlorophenylthio)-(2,3,5-tri-O-acetyl-β-D-ribofuran-osyl)purine 11, which is readily prepared by allowing the corresponding 6-chloro-compound 10 to react with 4-chloro(thiophenol) and triethylamine in methanol solution at room temperature, reacts with boron trifluoride diethyl etherate in boiling dichloromethane solution to give 2-amino-6-(4-chlorophenyl-thio)-9H-purine 12 in high isolated yield. 9-[(2-Acetoxyethoxy)methyl]-2-amino-6-(4-chlorophenylthio)-9H-purine 13, prepared from the latter aglycone 12 in good yield, is converted by a four-step process into acyclovir 1 and by a two-step process into 6-deoxyacyclovir 2.

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