470699-74-2

Upstream product

• 484678-85-5 methyl 5-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-methoxycarbonyl-α,β-D-ribo-pentofuranoside 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 208175-44-4 4-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-cytidine 

Downstream Products

• 470699-85-5 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-4-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphorylcytidine 
• 470699-84-4 5'-O-benzyl-4-N-(tert-butyloxycarbonyl)-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}cytidine 
• 470699-99-1 5'-O-benzyl-2'-deoxy-3'-O-diethylphosphoryl-4'α-{[(2-(2-iodophenyl)ethyl)thio]carbonyl}cytidine 
• 470700-00-6 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphorylcytidine 
• 470699-82-2 5'-O-benzyl-4-N-(tert-butyloxycarbonyl)-2'-deoxy-4'α-[(2-iodophenylethylthio)carbonyl]cytidine 
• 470699-83-3 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-4-N-(tert-butyloxycarbonyl)-2'-deoxycytidine 
• 470699-81-1 5'-O-benzyl-4-N-(tert-butyloxycarbonyl)-4'α-carboxyl-2'-deoxycytidine 
• 470699-80-0 5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-4-N-(tert-butyloxycarbonyl)-2'-deoxy-4'α-methoxycarbonylcytidine 

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.