69504-01-4

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 51600-12-5 5'-O-monomethoxytrityluridine 
• 65109-15-1 2'-O-t-Butyldimethylsilyl-5'-O-monomethoxytrityl-N⁶-benzoyluridin 
• 58-96-8 uridine 
• 14470-28-1 mono-4-methoxytrityl chloride 

Downstream Products

• 65109-15-1 2'-O-t-Butyldimethylsilyl-5'-O-monomethoxytrityl-N⁶-benzoyluridin 
• 75666-60-3 4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 133782-87-3 Methanesulfonic acid (2R,3R,4R,5R)-4-allyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 
• 133782-89-5 5'-O-(MMTr)-2'-O-(allyl)-3'-O-(phenoxythiocarbonyl)uridine 
• 133782-65-7 5-O-(MMTr)-3'-deoxy-3'-C,2'-O-((1-methyl)ethylene)uridine 
• 133782-86-2 5'-O-(MMTr)-2'-O-(allyl)uridine 
• 133782-88-4 1-(5'-O-(MMTr)-2'-O-(allyl)-3'-deoxy-3'-phenylseleno-β-D-xylofuranosyl)uracil 

Relevant academic research and scientific papers

Nucleosides, XXXVII. - Synthesis and Properties of 2'-O- and 3'-O-(tert-Butyldimethylsilyl)-5'-O-(4-methoxytrityl)- and 2',3'-Bis(O-tert-butyldimethylsilyl)ribonucleosides - Starting Materials for Oligoribonucleotide Syntheses

The synthesis of aminoacylated 5'-O-(4-methoxytrityl)ribonucleosides of adenosine (1), guanosine (9), cytidine (31), uridine (17), and 5,6-dihydrouridine (23) have been optimized and these compounds (4, 12, 33, 18 and 24) silylated by tert-butyldimethylsilyl chloride.The corresponding 2'- and 3'-mono-O- as well as 2',3'-bis-O-(tert-butyldimethylsilyl) derivatives have been isolated by combination of chromatographical methods and fractional crystallization procedures in preparative scale.The characterization of the newly synthesized compounds was achieved by UV and 13C-NMR spectra.

ISOMERIZATION OF tert-BUTYLDIMETHYLSILYL PROTECTING GROUPS IN RIBONUCLEOSIDES

The tert-butyldimethylsilyl group undergoes isomerization between O-2' and O-3' in ribonucleosides in solution.Isomerization is most rapid in protic solvents and extremely slow in such solvents as dry dimethyl sulfoxide, pyridine, oxolane, chloroform, or