5'-DMT-RIBO ADENOSINE (N-BZ) Chemical Properties

Density 

1.36

storage temp. 

Sealed in dry,2-8°C

form 

Solid

pka

7.87±0.43(Predicted)

color 

White to off-white

Safety Information

HS Code 

2933599590

5'-DMT-RIBO ADENOSINE (N-BZ) Usage And Synthesis

Uses

5'-O-DMT-Bz-rA is an intermediate for cyclic di-nucleotide compounds?synthesis[1].

Synthesis

The general procedure for the synthesis of the target compound (CAS: 129666-75-7) from 4,4'-dimethoxytrityl chloride (DMTrCl) and N6-benzoyl adenosine was as follows: to a pyridine solution (100 g, 269.3 mmol, 0.5 mmol) containing N-(9-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl) at 0 °C, N-(9-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl )-benzamide (100 g, 269.3 mmol) to a pyridine solution (500 mL) was added DMAP (1.64 g, 13.46 mmol, 0.05 equiv) and DMTrCl (100.4 g, 296.2 mmol, 1.1 equiv) in sequence. The reaction mixture was stirred at room temperature for 16 h. Upon completion of the reaction, the reaction was quenched by addition of methanol (500 mL). Volatiles were removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (elution gradient: 1/1 petroleum ether/ethyl acetate to 100% ethyl acetate) to afford N-(9-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzene Formamide, as a white foamy solid (150 g, 223 mmol, 83% yield).

References

[1] Boyu Zhong, et al. Cyclic di-nucleotide compounds and methods of use. Patent WO2017161349.

5'-DMT-RIBO ADENOSINE (N-BZ)(81246-82-4)Related Product Information

• Diphenyldimethoxysilane
• 1,1-Dimethoxyethane
• 5'-Deoxyadenosylcobalamin
• Adenosine
• 2,6-Dimethoxybenzaldehyde
• ADENOSINE 5'-TRIPHOSPHATASE
• Benzoyl chloride
• Vidarabine
• Dimethyldimethoxysilane
• Benzoyl peroxide
• Dimethoxymethane
• N6-benzoyl-3'-O-t-butyldiMethylsilyl-5'-O-(4,4'-diMethoxytrityl)-adenosine
• 5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine
• N2-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-3'-O-tert-butyldimethylsilyl guanosine
• 5'-O-DMT-2'-O-iBu-N-Bz-Guanosine
• N-BENZOYLADENOSINE
• 5'-DMT-RIBO ADENOSINE (N-BZ)