156939-39-8

Basic information

• Product Name: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-(4-nitrophenyl carbonate)
• CAS NO: 156939-39-8
• Molecular Formula: C38H35N3O11
• Molecular Weight: 709.709
• Mol File: 156939-39-8.mol

Chemical Properties

• CAS DataBase Reference: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-(4-nitrophenyl carbonate)(CAS DataBase Reference)
• NIST Chemistry Reference: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-(4-nitrophenyl carbonate)(156939-39-8)
• EPA Substance Registry System: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 3'-(4-nitrophenyl carbonate)(156939-39-8)

Safety Data

• Hazardous Substances Data: 156939-39-8(Hazardous Substances Data)

Upstream product

• 7693-46-1 4-Nitrophenyl chloroformate 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 

Downstream Products

• 291753-13-4 C₅₅H₆₅N₅O₁₃Si 
• 669013-15-4 (3-Amino-propyl)-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 669013-16-5 [3-((R)-4-Cyano-3-hydroxy-butyrylamino)-propyl]-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 669013-14-3 (3-{(R)-4-Cyano-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-butyrylamino}-propyl)-carbamic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 154495-12-2 C₄₂H₄₅N₅O₁₂ 

Relevant articles and documents

Synthesis and biophysical properties of carbamate-locked nucleic acid (LNA) oligonucleotides with potential antisense applications

Antisense oligonucleotides (ASOs) are becoming important drugs for hard to treat diseases. Modifications to their DNA backbones are essential to inhibit degradation in vivo, but they can reduce binding affinity to RNA targets. To address this problem we have combined the enzymatic resistance of carbamate (CBM) DNA backbone analogues with the thermodynamic stability conferred by locked nucleic acid sugars (LNA). Using a dinucleotide phosphoramidite strategy and automated solid phase synthesis, we have synthesised a set of oligonucleotides modified with multiple LNA-CBM units. The LNA sugars restore binding affinity to RNA targets, and in this respect LNA position with respect to the CBM linkage is important. Oligonucleotides containing carbamate flanked on its 5′and 3′-sides by LNA form stable duplexes with RNA and unstable duplexes with DNA, which is desirable for antisense applications. Carbamate-LNA modified oligonucleotides also show increased stability in the presence of snake venom and foetal bovine serum compared to LNA or CBM backbones alone.

A novel reagent for the chemical phosphorylation of oligonucleotides

A novel phosphoramidite reagent was developed to convert terminal hydroxyl groups of oligonucleotides into phosphate monoesters. The reagent's appearance as a solid foam is advantageous for its manipulation and handling in solid phase synthesis and improves its thermal stability.

Novel phosphorylation reagents for improved processes to convert terminal hydroxyl groups of oligonucleotides into phosphate monoesters

The present invention discloses novel phosphoramidite reagents for use in oligonucleotide synthesis. The present invention further discloses novel methods for the conversion of terminal hydroxyl groups of oligonucleotides into phosphate monoesters. By emp

Syntheses and binding studies of oligonucleotides containing N- hydroxycarbamate linkages: Potential DNA cleaving antisense oligomers

An efficient synthesis of N-hydroxycarbamate containing thymidine dimer 9 was accomplished and it was incorporated into automatic DNA syntheses to make thymidine 16mers T*-1, T*-2 and T*-3. Binding abilities of T*-1, T*-2 and T*-3 with poly (dA)-16mer were assayed by melting denaturation (Tm) studies of the corresponding duplexes. Iron binding ability of a thymidine oligomer with N-hydroxycarbamate linkages was studied by MALDI-MS. Nuclease stability assays showed that the modified oligonucleotides have enhanced resistance toward nuclease S1 (endonuclease) compared to natural oligonucleotides. (C) 2000 Elsevier Science Ltd.