Mitsunobu coupling of nucleobases and alcohols: an efficient, practical synthesis for novel nonsugar carbon nucleosides.
A simple facile synthesis of substituted purine derivatives has been developed by using Mitsunobu conditions for an alcohol and a respective nucleobase. A wide range of alcohols produces good to excellent yield (>90%). The resulting purine analogues show good regioselectivity with N-9 substitution as the dominant products in most of the cases. Application of diastereospecific alcohols reveals a complete inversion of the carbon stereogenic center giving a single diastereomer. More than two dozen novel nucleobase derivatives have been prepared in high yield.
Lu
Weibing
W
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Sengupta
Sujata
S
Petersen
Jeffrey L
JL
Akhmedov
Novruz G
NG
Shi
Xiaodong
X
D000438:Alcohols / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D006147:Guanine / Q000737:chemistry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*
D000438:Alcohols; D009705:Nucleosides; D006147:Guanine; D002244:Carbon