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5'-CHLORO-5'-DEOXYADENOSINE

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CAS:892-48-8
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5'-CHLORO-5'-DEOXYADENOSINE manufacturers

5'-CHLORO-5'-DEOXYADENOSINE Basic information
Product Name:5'-CHLORO-5'-DEOXYADENOSINE
Synonyms:5'-CHLORO-5'-DEOXYADENOSINE;5-CHLORO-5-DEOXYADENOSINE HYDRATE;5'-CHLORO-5'-DEOXYADENOSINE MONOHYDRATE;5’-chloro-5’-deoxy-adenosin;5'-CHLORO-5'-DEOXY-D-ADENOSINE;5'-Deoxy-5'-chloroadenosine;5'-Cl-5'-deoxyadenosine;Adenosine,5'-chloro-5'-deoxy-
CAS:892-48-8
MF:C10H12ClN5O3
MW:285.69
EINECS:
Product Categories:
Mol File:892-48-8.mol
5'-CHLORO-5'-DEOXYADENOSINE Structure
5'-CHLORO-5'-DEOXYADENOSINE Chemical Properties
Melting point 187 °C (exothermic decomp onset @144.5 C)(lit.)
Boiling point 645.6±65.0 °C(Predicted)
density 2.03±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,2-8°C
solubility DMSO (Slightly), Water (Slightly, Heated)
form Solid
pka13.03±0.70(Predicted)
color Off-White to Light Beige
InChIInChI=1S/C10H12ClN5O3/c11-1-4-6(17)7(18)10(19-4)16-3-15-5-8(12)13-2-14-9(5)16/h2-4,6-7,10,17-18H,1H2,(H2,12,13,14)/t4-,6-,7-,10-/m1/s1
InChIKeyIYSNPOMTKFZDHZ-KQYNXXCUSA-N
SMILESC(Cl)[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@H](O)[C@@H]1O
Safety Information
WGK Germany 3
RTECS AU7357200
MSDS Information
ProviderLanguage
SigmaAldrich English
5'-CHLORO-5'-DEOXYADENOSINE Usage And Synthesis
Uses5''-Deoxy-5''-chloroadenosine is an intermediate in the synthesis of 5''-Deoxy-5''-(methylthio)adenosine (D242600), a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways.
DefinitionChEBI: 5'-chloro-5'-deoxyadenosine is a member of adenosines. It is functionally related to an adenosine.
Synthesis
Adenosine

58-61-7

5'-CHLORO-5'-DEOXYADENOSINE

892-48-8

General steps: 1. Preparation of (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-(chloromethyl) tetrahydrofuran-3,4-diol Under ice bath cooling conditions, (2R,3R,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (1 g, 3.47 mmol) was dissolved in acetonitrile (10 ml), pyridine (593 mg, 0.6 ml, 7.49 mmol) and SOCl2 (2.22 g, 1.36 ml, 18.65 mmol). The reaction mixture was stirred at 0-5 °C for 3-4 h, followed by slow warming to room temperature and stirring overnight. After completion of the reaction, the suspension was concentrated in vacuum. Methanol (20 ml), water (2 ml) and NH4OH (4 ml) were added to the concentrate and stirred for 0.5 h at room temperature. The reaction mixture was again concentrated to dryness. The crude product was dissolved in methanol, silica gel (3 g) was added and the solvent was subsequently removed. The residue was purified by silica gel column chromatography (SGC) using gradient elution with ethyl acetate:methanol (0%-10%) to afford the target compound (0.915 g, 86% yield) as a light yellow solid. NMR (500 MHz, MeOD): δ 8.24 (s, 1H), 8.02 (s, 1H), 7.27-7.20 (m, 5H), 6.19 (d, J = 2.0 Hz, 1H), 5.48-5.46 (m, 1H), 5.08-5.06 (m, 1H), 4.43 (t, J = 4.0 Hz, 1H), 3.83 -3.81 (m, 2H), 3.01-2.99 (br s, 2H), 1.60 (s, 3H), 1.38 (s, 3H) ppm. LCMS (m/z): 395.8 [M + H]+.

References[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 18, p. 8066 - 8074,9
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 46, p. 14277 - 14280
[3] Angew. Chem., 2016, vol. 128, # 46, p. 14489 - 14492,4
[4] Tetrahedron Letters, 2018, vol. 59, # 4, p. 415 - 417
[5] Patent: US4373097, 1983, A
Tag:5'-CHLORO-5'-DEOXYADENOSINE(892-48-8) Related Product Information
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