2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9--D-RIBOFURANOSIDE

Product Name: 2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9--D-RIBOFURANOSIDE
CAS No.: 5987-73-5
Chemical Name: 2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9--D-RIBOFURANOSIDE
Synonyms: NSC 281799;Adenosine Related Compound 5;6-Chloropurine riboside triacetate;2',3',5'-O-triacetyl-6-chloroinosine;2',3',5'-O-triacetyl-6-chloroinosine;2',3',5'-Tri-O-acetyl-6-chloronebularine;2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9-?-D-RIBOFURANOSIDE;2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside;6-Chloro-9-(2,3,5-tri-O-acetyl-β-D- ribofuranosyl)purine;9-(2',3',5'-Tri-O-acetyl-b-D-ribofuranosyl)-6-chloropurine
CBNumber: CB9649956
Molecular Formula: C16H17ClN4O7
Formula Weight: 412.78
MOL File: 5987-73-5.mol

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2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9--D-RIBOFURANOSIDE Property

Melting point:: 161-162°C
Boiling point:: 560.9±60.0 °C(Predicted)
Density: 1.62±0.1 g/cm3(Predicted)
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
solubility: Chloroform, Methanol (Sparingly)
form: Oil
pka: 0.76±0.10(Predicted)
color: Light Yellow
optical activity: -19.23°(C=1.00g/100mL, MEOH, 589nm)
InChI: InChI=1/C16H17ClN4O7/c1-7(22)25-4-10-12(26-8(2)23)13(27-9(3)24)16(28-10)21-6-20-11-14(17)18-5-19-15(11)21/h5-6,10,12-13,16H,4H2,1-3H3/t10-,12-,13-,16-/s3
InChIKey: INOTYVPMBNDAFK-UARIJUISNA-N
SMILES: O1[C@@H](N2C3C(=C(Cl)N=CN=3)N=C2)[C@H](OC(=O)C)[C@H](OC(=O)C)[C@H]1COC(C)=O |&1:1,12,17,22,r|

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC

Product number: T736250
Product name: 2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside(~90%)
Packaging: 500mg
Price: $50
Updated: 2021/12/16

TRC

Product number: T736250
Product name: 2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside(~90%)
Packaging: 1g
Price: $80
Updated: 2021/12/16

Biosynth Carbosynth

Product number: NT10156
Product name: 9-(2',3',5'-Tri-O-acetyl-b-D-ribofuranosyl)-6-chloropurine
Packaging: 2g
Price: $80
Updated: 2021/12/16

Biosynth Carbosynth

Product number: NT10156
Product name: 9-(2',3',5'-Tri-O-acetyl-b-D-ribofuranosyl)-6-chloropurine
Packaging: 5G
Price: $100
Updated: 2021/12/16

AK Scientific

Product number: 8922AB
Product name: (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyldiacetate
Packaging: 1g
Price: $117
Updated: 2021/12/16

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2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9--D-RIBOFURANOSIDE Chemical Properties,Usage,Production

Chemical Properties

Colourless Crystalline Powder

Uses

2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside is a nucleoside compound with inhibitory activity on a rho-GTPase cell protein.

Synthesis

3181-38-2

5987-73-5

GENERAL STEPS: (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-oxo-1H-purin-9(6H)-yl)tetrahydrofuran-3,4-diyl diacetate (5.00 g, 12.68 mmol, 1.00 eq.), benzyltriethylammonium chloride (5.77 g, 25.36 mmol, 2.00 eq.) and N,N- dimethylaniline (1.8 mL, 13.94 mmol, 1.10 equiv) were dissolved in 50 mL of anhydrous acetonitrile. The reaction mixture was placed in a preheated oil bath (70°C) and trichlorophosphorus (5.9 mL, 63.40 mmol, 5.00 eq.) was slowly added dropwise and stirred at the same temperature for 2 hours. After completion of the reaction, the solvent and the remaining phosphorous trichloride were removed under reduced pressure (high vacuum, 70°C). The residue was poured into a chloroform/ice mixture and stirred for 20 minutes. The organic phase was separated and the aqueous phase was extracted with chloroform three times. The organic phases were combined and washed with 5% sodium bicarbonate solution until the aqueous layer was weakly basic. Subsequently, the organic phases were separated, dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. Purification by silica gel column chromatography (eluent: ethyl acetate) afforded the target product (2R,3R,4R,5R)-2-(acetyloxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diacetic acid diester (Compound 17) as a yellow oil (5.23 g, quantitative yield).

References

[1] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 1563 - 1569
[2] Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 9, p. 603 - 611
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6736 - 6739
[4] Patent: WO2005/84653, 2005, A2. Location in patent: Page/Page column 42
[5] British Journal of Pharmacology, 2017, vol. 174, # 14, p. 2287 - 2301

2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9--D-RIBOFURANOSIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9--D-RIBOFURANOSIDE Suppliers

Canada 1 China 42 China Hong Kong 1 Germany 1 India 3 Switzerland 1 United Kingdom 3 United States 5 Global 57

Toronto Research Chemicals

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Email: info@trc-canada.com
Country: Canada
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View Lastest Price from 2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9--D-RIBOFURANOSIDE manufacturers

Career Henan Chemical Co

Product: 2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9-?-D-RIBOFURANOSIDE 5987-73-5
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98% HPLC
Supply Ability: 10 tons
Release date: 2020-03-04

5987-73-5, 2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9--D-RIBOFURANOSIDERelated Search:

6-Chloropurine (R, S)-Adenosyl-L-Methionine ADENOSINE 5'-TRIPHOSPHATE DISODIUM SAL& Adenosine-5'-diphosphate disodium salt 4'-ethynyl-2-fluoro-2'-deoxyadenosine ADENOSINE5'-MONOPHOSPHATESODIUMSALT 8-AMino[1”-(N”-dansyl)-4”-aMinobutyl]-5'-(1-aziridinyl)-5'-deoxy Adenosine Ademetionine 1,4-butanedisulfonate (S, S)-Adenosyl-L-Methionine Decarboxy-S-adenosylmethionine 5'-DEOXY-5'-METHYLTHIOADENOSINE S-Adenosyl-L-methionine Adenosine 5'-monophosphate S-Adenosyl-L-methionine Disulfate Tosylate 2-methylthio-N-6-isopentenyladenosine Adenosine-13C5 2'-O-MB-CAMP SODIUM SALT Adenosine Related Compound 1

2',3',5'-O-triacetyl-6-chloroinosine

2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9-?-D-RIBOFURANOSIDE

9-(2',3',5'-Tri-O-acetyl-b-D-ribofuranosyl)-6-chloropurine

2',3',5'-Tri-O-acetyl-6-chloronebularine

6-Chloro-9-(2,3,5-tri-O-acetyl-β-D- ribofuranosyl)purine

6-Chloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine

6-Chloro-9-β-D-ribofuranosyl-9H-purine 2',3',5'-Triacetate

NSC 281799

9-(2',3',5'-Tri-O-acetyl-beta-D-ribofuranosyl)-6-chloropurine

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate

6-Chloro-9-(2',3',5'-tri-O-acetyl-beta-D-ribofuranosyl)purine

6-Chloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine

6-Chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine

2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside (~90%)

Adenosine Related Compound 5

2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside

9H-Purine, 6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-

(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(6-chloro-9H-purin-9-yl)oxolan-2-yl]methyl acetate

[3,4-BIS(ACETYLOXY)-5-(6-CHLOROPURIN-9-YL)OXOLAN-2-YL]METHYL ACETATE

2',3',5'-O-triacetyl-6-chloroinosine

6-Chloropurine riboside triacetate

9-(2',3',5'-Tri-O-acetyl-β-D-ribofuranosyl)-6-chloropurine

2,3,5-Tri-O-acetyl-6-chloropurine-9-beta-D-ribofuranoside (~90%)

5987-73-5

C16H17ClN4O7

Bases & Related Reagents

Nucleotides

Carbohydrates & Derivatives