2-CHLORO-9-(2,3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYL)ADENINE Chemical Properties

Melting point:

186-187°C

Boiling point:

556.1±60.0 °C(Predicted)

Density 

1.90±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

soluble in Acetone, DMF, DMSO, Methanol

form 

Solid

pka

14.14±0.10(Predicted)

color 

White

2-CHLORO-9-(2,3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYL)ADENINE Usage And Synthesis

Chemical Properties

White Soild

Uses

nucleoside analogue

Synthesis

The reaction of 2-chloroadenosine (Ila, 20 g, 66.3 mmol), 2,2-dimethoxypropane (DMOP, 60 mL) and 70% wt aqueous hydrochloric acid solution (3 mL) was stirred at room temperature for 8 h under nitrogen atmosphere. Subsequently, the pH of the reaction mixture was adjusted to 7-9 by slow addition of saturated aqueous sodium bicarbonate solution (about 120 mL). the mixture was stirred in an ice bath for 2 h. The mixture was subjected to filtration, and the filter cake was washed with water (50 mL), followed by drying under vacuum at 50 °C for 6 h to afford the title compound (Formula 11b) with 99% purity and 88% yield. The product was characterized by 1H NMR (400 MHz, DMSO-d6) and 13C NMR (100 MHz, DMSO-d6) with the following data: 1H NMR δ 8.36 (s, 1H), δ 7.87 (s, 2H), δ 6.06 (d, J = 2.4 Hz, 1H), δ 5.28 (dd, J = 6 Hz, 2.4 Hz, 1H), δ 5.08 (t, J = 5.6Hz, 1H), δ4.94 (dd, J = 6Hz, 2Hz, 1H), δ4.21 (m, 1H), δ3.54 (m, 2H), δ1.54 (s, 3H), δ1.33 (s, 3H); 13C NMR δ157.3, 153.6, 150.4, 140.4, 118.6, 113.6, 89.8, 87.2, 83.9, 81.7, 62.0, 27.5, 25.7.

References

[1] Nucleosides and Nucleotides, 1999, vol. 18, # 10, p. 2175 - 2191
[2] Patent: WO2015/85497, 2015, A1. Location in patent: Paragraph 0041-0044
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 15, p. 4556 - 4560
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 85 - 89
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 7, p. 1919 - 1924

2-CHLORO-9-(2,3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYL)ADENINE(24639-06-3)Related Product Information

• 2-CHLORO-9-(2-3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYLURONIC ACID)ADENINE
• 2-Chloroadenosine
• Cladribine
• 2',3'-O-Isopropylideneadenosine
• 2-chloro-2',3'-dideoxyadenosine
• 2-CHLORO-9-(2,3-O-ISOPROPYLIDENE-BETA-D-RIBOFURANOSYL)ADENINE