223923-96-4Relevant academic research and scientific papers
Asymmetric synthesis of C4'α-carboxylated 2'-deoxynucleosides. Preparation of oxetanone derivatives and influence of solvent on the stereochemistry of base introduction
Crich, David,Hao, Xiaolin
, p. 4016 - 4024 (2007/10/03)
A synthesis of methyl 5-O-benzyl-3-O-tert-butyldimethylsilyl-4α- methoxycarbonyl-2-deoxyribofuranoside from dimethyl L-tartrate is presented. Coupling of this substance with standard purine and pyrimidine bases, promoted by tin tetrachloride, provides the corresponding 4'α- methoxycarbonyl-nucleosides with moderate yield and selectivity. A series of related bicyclic donors, derived by forming a β-lactone between the 3-OH and the 4α-carboxy group, were prepared and assayed in coupling reactions. In nonpolar solvents good endo-selectivity is observed whereas in acetonitrile the exo-anomers are preferentially obtained. Methods for the removal of the 5'-O-benzyl ethers of the nucleosides are presented.
