208175-26-2

Upstream product

• 931-94-2 1,1-dimethoxycyclopentane 
• 608-68-4 dimethyl L-tartrate 
• 3587-60-8 Benzyloxymethyl chloride 
• 198691-38-2 dimethyl 2,3-O-cyclopentylidene-L-tartrate 

Downstream Products

• 208175-36-4 2R,3S-2-benzyloxymethyl-3-<2,2-di(methoxy)ethyl>-2-methoxycarbonyl-1,4-dioxaspiro<4.4>nonane 
• 208175-30-8 2R,3R-2-benzyloxymethyl-2-methoxycarbonyl-1,4-dioxaspiro<4.4>nonane-3-carboxaldehyde 
• 208175-28-4 2R,3S-2-benzyloxymethyl-3-hydroxymethyl-2-methoxycarbonyl-1,4-dioxaspiro<4.4>nonane 

Relevant 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

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.