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| | 6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine Basic information |
| Product Name: | 6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine | | Synonyms: | 6-CHLORO-9-[2.3-0-(ISOPROPYLIDENE)-BETA-D-RIBOFURONOSYL]-9H-PURINE;6-Chloro-9-[2,3-o-(Isopropylid;6-Chloro-9-(2',3'-O-isopropylidene-b-D-ribofuranosyl)purine;6-chloro-9-[230-(isopropylidene)--D-ribofuronosyl]-9H-purine;6-CHLORO-9-[2,3-O-(ISOPROPYLIDENE)-SS-D-RIBOFURONOSYL]-9H-PURINE;6-CHLORO-9-BETA-D-(2,3-ISOPROPYLIDENE)RIBOFURANOSYLPURINE;6-CHLORO-9-[2,3-O-(ISOPROPYLIDENE)-BETA-D-RIBOFURONOSYL]-9H-PURINE;6-CHLOROPURINE-9-(2,3-ISOPROPYLIDENE-B-D-RIBOFURANOSIDE) | | CAS: | 39824-26-5 | | MF: | C13H15ClN4O4 | | MW: | 326.74 | | EINECS: | | | Product Categories: | Bases & Related Reagents;Nucleotides | | Mol File: | 39824-26-5.mol |  |
| | 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) | | form | Solid | | pka | 14.14±0.10(Predicted) | | color | Pale Yellow | | Optical Rotation | 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 Preparation Products And Raw materials |
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