114522-12-2

Basic information

• Product Name: Uridine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-4-O-[2-(4-nitrophenyl)ethyl]-
• CAS NO: 114522-12-2
• Molecular Formula: C38H37N3O10
• Molecular Weight: 695.726
• Mol File: 114522-12-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Uridine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-4-O-[2-(4-nitrophenyl)ethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Uridine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-4-O-[2-(4-nitrophenyl)ethyl]-(114522-12-2)
• EPA Substance Registry System: Uridine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-4-O-[2-(4-nitrophenyl)ethyl]-(114522-12-2)

Safety Data

• Hazardous Substances Data: 114522-12-2(Hazardous Substances Data)

Usage

General Description

The chemical Uridine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-4-O-[2-(4-nitrophenyl)ethyl]- is a modified form of the nucleoside uridine. It is a compound with a complex structure, containing multiple phenyl and nitro groups attached to the uridine molecule. This chemical modification can potentially alter the biological and pharmacological properties of uridine, potentially affecting its ability to interact with various enzymes, receptors, and transporters in the body. Research into the specific effects and potential applications of this modified uridine compound is ongoing.

Upstream product

• 4105-38-8 Tri-O-acetyluridine 
• 116980-91-7 2',3',5'-tri-O-acetyl-O⁴-<2-(4-nitrophenyl)ethyl>uridine 
• 40615-36-9 4,4'-dimethoxytrityl chloride 
• 173169-06-7 O⁴-<2-(4-nitrophenyl)ethyl>uridine 
• 82913-19-7 [(2R,3R,4R)-3,4-diacetoxy-5-[2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]tetrahydrofuran-2-yl]methyl acetate 
• 20264-96-4 2-(4-nitrophenyl)ethyl iodide 
• 100-27-6 2-(4-nitrophenyl)ethanol 

Downstream Products

• 114522-13-3 5'-O-(dimethoxytrityl)-O⁴-<2-(4-nitrophenyl)ethyl>-3'-O-<2-(4-nitrophenyl)ethylsulfonyl>uridine 
• 173169-64-7 3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(dimethoxytrityl)-O⁴-<2-(4-nitrophenyl)ethyl>uridine 

Relevant articles and documents

Nucleosides. Part LIX. The 2-(4-nitrophenyl)ethylsulfonyl (Npes) group: A new type of protection in nucleoside chemistry

The 2-(4-nitrophenyl)ethylsulfonyl (npes) group is developed as a new sugar OH-blocking group in the ribonucleoside series. Its cleavage can be performed in a β-eliminating process under aprotic conditions using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the most effective base. Since sulfonates do not show acyl migration, partial protection of 1,2-cis-diol moieties is possible leading to new types of oligonucleotide building blocks. A series of Markiewicz-protected ribonucleosides 1-10 is converted into their 2'-O-[2-(4-nitrophenyl)ethylsulfonyl] derivatives 29-38 in which the 5'-O-Si bond can be cleaved by acid hydrolysis forming 39-45. Subsequent monomethoxytritylation leads to 46-50, and desilylation affords the 5'-O-(monomethoxytrityl)-2'-O-[2-(4-nitrophenyl)ethylsulfonyl]ribonucl eosides 51-55. Acid treatment to remove trityl groups do also not harm the npes group(→ 56-58). Unambiguous syntheses of fully blocked 2'-O-[2-(4-nitrophenyl)ethylsulfonyl]ribonucleosides 96-102 are achieved from the corresponding 3'-O-(tert-butyl)dimethylsilyl derivatives. Furthermore, various base-protected 5'-O-(monomethoxytrityl)- and 5'-O-(dimethoxytrityl)ribonucleosides, i.e. 59-77, are treated directly with 2-(4-nitrophenyl)ethylsulfonyl chloride forming in all cases a mixture of the 2',3'-di-O- and the two possible 2'- and 3'-O-monosulfonates 107-148 which can be separated into the pure components by chromatographic methods. The npes group is more labile towards DBU cleavage than the corresponding base-protecting 2-(4-nitrophenyl)ethyl (npe) and 2-(4-nitrophenyl)ethoxycarbonyl (npeoc) groups allowing selective deblocking which is of great synthetic potential.