208175-46-6

Basic information

• Product Name: 2-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-guanosine
• Synonyms: 2-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-guanosine
• CAS NO: 208175-46-6
• Molecular Weight: 571.706
• Mol File: 208175-46-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-guanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-guanosine(208175-46-6)
• EPA Substance Registry System: 2-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-guanosine(208175-46-6)

Safety Data

• Hazardous Substances Data: 208175-46-6(Hazardous Substances Data)

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 19962-37-9 N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide 
• 484678-85-5 methyl 5-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-methoxycarbonyl-α,β-D-ribo-pentofuranoside 

Relevant articles and documents

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.