2',3'-O-Isopropylideneinosine Chemical Properties

Melting point:

263-272°C

Boiling point:

606.6±65.0 °C(Predicted)

Density 

1.80±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)

form 

Solid

pka

14.14±0.10(Predicted)

color 

White to Off-White

InChI

InChI=1S/C13H16N4O5/c1-13(2)21-8-6(3-18)20-12(9(8)22-13)17-5-16-7-10(17)14-4-15-11(7)19/h4-6,8-9,12,18H,3H2,1-2H3,(H,14,15,19)/t6-,8-,9-,12-/m1/s1

InChIKey

LIEKLUBCIPVWQD-WOUKDFQISA-N

SMILES

OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)O)N=C2)[C@@H]2OC(O[C@H]12)(C)C

CAS DataBase Reference

2140-11-6(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29389090

MSDS

• Language:English Provider:SigmaAldrich

2',3'-O-Isopropylideneinosine Usage And Synthesis

Chemical Properties

2',3'-O-Isopropylideneinosine is White Solid

Uses

2',3'-O-Isopropylideneinosine is an inosine derivative as antiviral, bactericidal, and antitumor agent for immunopotentiating uses.

Uses

A useful precursor for the preparation of nucleic acids

Synthesis

To a solution of inosine (0.998 g, 3.72 mmol) in dimethylformamide (DMF, 30 mL) was sequentially added 2,2-dimethoxypropane (1.8 mL, 14.59 mmol) and p-toluenesulfonic acid monohydrate (0.038 g, 0.372 mmol). The reaction mixture was stirred under argon (Ar) protection for 24 hours. Upon completion of the reaction, DMF was removed by evaporation under reduced pressure, followed by alkalinization of the reaction mixture with 3% ammonia solution and evaporation again to dryness. The resulting residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol, 95/5, v/v) to afford the target compound 22 in white foamy form in 80% yield. The product was characterized by 1H-NMR (200 MHz, DMSO-d6): δ 1.34, 1.50 (6H, s, (CH3)2C), 3.6 (2H, t, CH2-5'), 4.37 (1H, m, H-4'), 4.94 (1H, m, H-3'), 5.18 (1H, t, OH-5'), 5.37 (1H, dd. J = 3.7 Hz, H-2'), 6.12 (1H, d, J = 2.4 Hz, H-1'), 8.05 (1H, s, H-2), 8.32 (1H, s, H-8), and 12.44 (1H, br s, NH-3).ESI-MS analysis showed: m/z 309.1 [M + H]+, molecular formula C13H16N4O5, molecular weight 308.29.

References

[1] European Journal of Medicinal Chemistry, 2012, vol. 54, p. 202 - 209
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 5, p. 2087 - 2103
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 17, p. 5349 - 5370
[4] Heterocycles, 2013, vol. 87, # 11, p. 2369 - 2384
[5] Chinese Chemical Letters, 2011, vol. 22, # 12, p. 1439 - 1442

2',3'-O-Isopropylideneinosine(2140-11-6)Related Product Information

• Mesityl oxide
• Disodium 5'-Inosinate
• Isoprinosine
• Dideoxyinosine
• 6-Hydroxypurine
• 3-Isopropoxypropylamine
• 2'-Deoxyinosine
• 1-METHYL-1H-IMIDAZOLE-4-CARBALDEHYDE
• (1-Methyl-1H-imidazol-4-yl)methylamine
• (S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol
• AICAR
• 2',3'-O-Isopropylideneguanosine
• Inosine
• 1,3-Dioxolane-4-methanol
• 2,2-Dimethyl-1,3-dioxolane-4-methanol
• [(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methanamine
• 2',3'-O-ISOPROPYLIDENE-5'-TRITYLINOSINE
• 5-AMINO-1-PROPYL-1H-IMIDAZOLE-4-CARBOXAMIDE