799773-85-6

Upstream product

• 854864-70-3 2, 7-dimethyl-9-phenyl xanthen-9-ol 
• 51009-90-6 2,7-dimethyl-9-phenyl-xanthene 
• 65-85-0 benzoic acid 
• 1579-40-4 1,1'-oxybis(4-methyl-benzene) 
• 1411696-46-2 DMPx-OMe 
• 7573-15-1 2,7-dimethylxanthen-9-one 

Downstream Products

• 1520896-18-7 C₄₉H₅₅N₈O₆P 
• 1520896-72-3 C₄₃H₅₁N₈O₆P 
• 1520896-36-9 C₃₄H₃₄N₆O₅ 
• 1520896-39-2 C₃₂H₃₁N₃O₆ 
• 1520896-11-0 C₃₈H₃₆N₆O₆ 
• 1520896-13-2 C₄₇H₅₃N₈O₇P 
• 1520896-16-5 C₄₀H₃₈N₆O₅ 
• 1520896-23-4 C₄₁H₃₇N₇O₅ 
• 1520896-25-6 C₅₀H₅₄N₉O₆P 

Relevant academic research and scientific papers

Utility of 5'-o-2,7-dimethylpixyl for solid-phase synthesis of oligonucleotides containing acid-sensitive 8-aryl-guanine adducts

To study the structural and biological impact of 8-aryl-2'-deoxyguanosine adducts, an efficient protocol is required to incorporate them site-specifically into oligonucleotide substrates. Traditional phosphoramidite chemistry using 5'- O-DMT protection can be limiting because 8-aryl-dG adducts suffer from greater rates of acid-catalyzed depurination than dG and are sensitive to the acidic deblock conditions required to remove the DMT group. Herein we show that the 5'-O-2,7- dimethylpixyl (DMPx) protecting group can be used to limit acid exposure and improve DNA synthesis efficiency for DNA substrates containing 8-aryl-dG adducts. Our studies focus on 8-aryl-dG adducts with 8-substituents consisting of furyl (FurdG), phenyl (PhdG), 4-cyanophenyl (CNPhdG), and quinolyl (QdG). These adducts differ in ring size and sensitivity to acid-promoted deglycosylation. A kinetic study for adduct hydrolysis in 0.1 M aqueous HCl determined that FurdG was the most acid-sensitive (55.2-fold > dG), while QdG was the most resistant (5.6-fold > dG). The most acid-sensitive FurdG was chosen for optimization of solid-phase DNA synthesis. Our studies show that the 5'-O-DMPx group can provide a 4-fold increase in yield compared to 5'- O-DMT for incorporation of FurdG into DNA substrates critical for determining adduct impact on DNA synthesis and repair.

Scalable synthesis of substituted 2,7-dimethyl-9-phenylxanthen-9-ol (DMPx-OH): Useful for the preparation of crystalline 5′-O-DMPx-protected nucleosides

A convenient single-step synthesis of several 2,7-dimethyl-9-phenylxanthen- 9-ol (DMPx-OH) analogs has been accomplished using a Friedel-Crafts reaction. Treatment of various DMPx-OH with unprotected 2′-O-methoxyethyl- ribonucleosides (MOE) in the presence of B(C6F5) 3, as a Lewis Acid catalyst, furnished 5′-O-protected derivatives of 2′-MOE-ribonucleosides in good yields. The deprotection of the DMPx groups was accomplished by acid hydrolysis under very mild conditions. Among the five DMPx analogs synthesized, the 2,7-dimethyl-9-(4-nitrophenyl) xanthene-9-yl group furnished crystalline products enabling non-chromatographic isolation of 5′-O-protetced nucleosides.

SUBSTITUTED PIXYL PROTECTING GROUPS FOR OLIGONUCLEOTIDE SYNTHESIS

The present invention describes an improved hydroxyl protecting group of formula (1), wherein R2 and R7 are specified substituents and Q is O, S, NR10 or N(C=O)R10.