| Identification | More | [Name]
6-Chloro-9-beta-D-(2,3-isopropylidene)ribofuranosylpurine | [CAS]
39824-26-5 | [Synonyms]
6-CHLORO-9-[2,3-O-(ISOPROPYLIDENE)-BETA-D-RIBOFURONOSYL]-9H-PURINE
6-CHLORO-9-BETA-D-(2,3-ISOPROPYLIDENE)RIBOFURANOSYLPURINE
6-CHLOROPURINE-9-(2,3-ISOPROPYLIDENE-B-D-RIBOFURANOSIDE)
6-CHLOROPURINE-9-(2,3-ISOPROPYLIDENE-BETA-D-RIBOFURANOSIDE)
6-Chloropurine-9-(2,3-isopropylidene)-b-d-ribfuraniside
6-CHLORO-9-[2,3-O-(ISOPROPYLIDENE)-β-D-RIBOFURONOSYL]-9H-PURINE
6-Chloro-9-b-D-(2,3-isopropylidene)ribofuranosylpurine
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-[2'',3''-0-(ISOPROPYLIDENE)-SS-D-RIBOFURONOSYL]-9H-PURINE
6-Chloro-9--D-(2,3-isopropylidene)ribofuranosylpurine
6-Chloropurine-9-(2,3-isopropylidene--D-ribofuranoside) | [Molecular Formula]
C13H15ClN4O4 | [MDL Number]
MFCD03788833 | [Molecular Weight]
326.74 | [MOL File]
39824-26-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale Yellow Solid | [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) |
| Hazard Information | Back Directory | [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 |
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