6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine Chemical Properties

Melting point:

156-159°C

Boiling point:

527.8±60.0 °C(Predicted)

Density 

1.79±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), Dichloromethane (Slightly), Diethyl Ether (Slightly)

pka

14.14±0.10(Predicted)

form 

Solid

color 

Pale Yellow

optical activity

Consistent with structure

CAS DataBase Reference

39824-26-5(CAS DataBase Reference)

6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

6-Chloropurine-9-(2,3-isopropylidene-β-D-ribofuranoside) (cas# 39824-26-5) is a compound useful in organic synthesis.

Synthesis

Synthesis of (((3aR,4R,6R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol from (3R,4S,5R)-2-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl) and acetone The general procedure was as follows: to a stirred suspension of anhydrous acetone (300 mL) of (3R,4S,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (3.0 g, 10.5 mmol) was added to toluenesulfonic acid monohydrate (19.8 g, 104 mmol). the solid was completely solubilized after 15 minutes. After 2 hours of reaction, the reaction solution was slowly poured into a stirred aqueous 0.5 N NaHCO3 solution (300 mL). After removing the acetone under vacuum, the mixture was extracted with dichloromethane (DCM, 100 mL x 5). The organic layers were combined, washed sequentially with water (100 mL) and brine (100 mL), dried over anhydrous Na2SO4, filtered and concentrated to give the target product (3.0 g, 87% yield, purity >96%) as a pale white solid. The product was characterized by 1H NMR (500 MHz, CD3OD) and LCMS (m/z: 327.1 [M+1]+).

References

[1] Nucleosides and Nucleotides, 1996, vol. 15, # 1-3, p. 619 - 629
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 7, p. 3848 - 3865
[3] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 8, p. 577 - 582
[4] Patent: WO2012/82436, 2012, A2. Location in patent: Page/Page column 192-193
[5] Patent: WO2012/82436, 2012, A2. Location in patent: Page/Page column 256-257

6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine(39824-26-5)Related Product Information

• 6-Chloro-9-(2-O-acetyl-5-O-benzoyl-3-azido-3-deoxy-beta-D-ribofuranosyl)-9H-purine
• 6-Chloro-9-[2-O-acetyl-5-O-(p-toluoyl)-3-azido-3-deoxy-beta-L-ribofuranosyl]-9H-purine
• 6-Chloro-9-(3,5-di-O-acetyl-2-O-methyl-β-D-ribofuranosyl)-9H-purine
• Trichloroisocyanuric acid
• DMT-dT Phosphoramidite
• DMT-dC(bz) Phosphoramidite
• DMT-dG(ib) Phosphoramidite
• DMT-dA(bz) Phosphoramidite
• DMT-dG(dmf) Phosphoramidite
• 2',3'-O-Isopropylideneadenosine
• 6-Chloropurine
• 6-CHLORO-9-(5-DEOXY-D-RIBOFURANOSYL)PURINE
• 6-Chloropurine ribonucleoside
• 6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine
• 6-CHLOROPURINE-2'-DEOXYRIBOSIDE