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Synthesis 2011(8): 1213-1218
DOI: 10.1055/s-0030-1259961
DOI: 10.1055/s-0030-1259961
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
An Efficient Approach for the Synthesis of 1′-O-α-Methyl Pyrrolo[2,3-d]pyrimidine Isonucleosides
Further Information
Received
26 December 2010
Publication Date:
16 March 2011 (online)
Publication History
Publication Date:
16 March 2011 (online)
![](https://www.thieme-connect.de/media/synthesis/201108/lookinside/thumbnails/10.1055-s-0030-1259961-1.jpg)
Abstract
A series of novel 1′-O-α-methyl isonucleosides were efficiently and stereoselectively synthesized with 1,2,3,5-tetra-O-acetyl-d-ribofuranose as the starting material. The key steps include regioselective and stereoselective deprotection of the 2,4-dichlorobenzyl group at C2, triflation, and substitution with appropriate nucleobases using cesium carbonate as the base. Removal of the residual 2,4-dichlorobenzyl groups and subsequent transformation afforded the title compounds in 30-37% overall yield. The products represent a new type of isonucleosides with 1′-O-substitution.
Key words
pyrrolo[2,3-d]pyrimidine - isonucleoside - regioselective deprotection - triflate - cesium carbonate
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- Supporting Information
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