5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine Chemical Properties

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

7.87±0.43(Predicted)

form 

Solid

color 

White to off-white

InChIKey

DAZIGOPASNJPCJ-OLXVHECFNA-N

SMILES

O(C(C1=CC=C(OC)C=C1)(C1=CC=C(OC)C=C1)C1=CC=CC=C1)C[C@H]1O[C@@H](N2C3=C(C(=NC=N3)NC(=O)C3=CC=CC=C3)N=C2)[C@H](O[Si](C(C)(C)C)(C)C)[C@@H]1O |&1:25,27,46,55,r|

5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine Usage And Synthesis

Uses

5''-O-DMT-2''-O-TBDMS-N-Bz-Adenosine (CAS# 81265-93-2) is a fluorescent adenosine-containing compound which is often used in for DNA/RNA modifications for detection or the addition of synthetic oligonucleotide blocks.

Synthesis

Synthesis of N-(9-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)-3-hydroxytetrahydrofuran-2-yl)-9H-purin-6-yl)benzamide from compound (CAS:129666-75-7) and tert-butyldimethylsilylene and the The general procedure for the compound (CAS:129681-71-6) was as follows: to a solution of tetrahydrofuran (THF, 800 mL) and pyridine (15 mL) of the product of the previous step (200 g, 296.9 mmol) was added sequentially silver cyanide (AgNCb, 83.2 g, 489.8 mmol, 1.65 equiv) and tert-butyldimethylchlorosilane ( TBSCl, 78.7 g, 522.5 mmol, 1.76 equiv). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was filtered, diluted with water (H2O, 1.0 L) and extracted with ethyl acetate (EtOAc, 3 x 1.0 L). The organic layers were combined, washed with brine (2 × 1.0 L), dried over anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure. The residue was purified by silica gel (SiO2) column chromatography (eluent: petroleum ether/ethyl acetate=3/1 to 1/1) to afford the products D-2a (114 g, 145 mmol, 49% yield) and D-2b (53 g, 68 mmol, 23% yield).

References

[1] Patent: WO2018/156625, 2018, A1. Location in patent: Paragraph 0296
[2] Canadian Journal of Chemistry, 1982, vol. 60, p. 111 - 120

5'-O-DMT-2'-O-TBDMS-N-Bz-Adenosine(81265-93-2)Related Product Information

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• INDEX NAME NOT YET ASSIGNED
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