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

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate
• CAS No.: 5987-73-5
• Molecular Formula: C16H17 Cl N4 O7
• Molecular Weight: 412.787
• ChEMBL ID: CHEMBL4642822
• DSSTox Substance ID: DTXSID80473915
• Nikkaji Number: J1.153.918A
• Mol file: 5987-73-5.mol

Synonyms:5987-73-5;(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate;[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-chloropurin-9-yl)oxolan-2-yl]methyl acetate;C16H17ClN4O7;INOTYVPMBNDAFK-XNIJJKJLSA-N;SCHEMBL3853209;CHEMBL4642822;DTXSID80473915;MFCD09841351;AKOS016006107;DS-4220;(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyldiacetate;F12890;2,3,5-Tri-O-acetyl-6-chloropurine-9- beta -D-ribofuranoside;6-Chloro-9-(2,3,5-tri-O-acetyl--D-ribofuranosyl)-9H-purine;6-chloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine;9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-chloropurine;2,3,5-TRI-O-ACETYL-6-CHLOROPURINE-9-?-D-RIBOFURANOSIDE;2,3,5-Tri-O-acetyl-6-chloropurine-9-?-D-ribofuranoside (~90%);2,3,5-Tri-O-acetyl-6-chloropurine-9-b-D-ribofuranoside (>90%);6-Chloro-9-(2,3,5-tri-O-acetyl-|A-D-ribofuranosyl)-9H-purine

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

Chemical Property:

• Vapor Pressure: 1.31E-12mmHg at 25°C
• Melting Point: 161-162°C
• Boiling Point: 560.9°C at 760 mmHg
• PKA: 0.76±0.10(Predicted)
• Flash Point: 293°C
• PSA: 131.73000
• Density: 1.62g/cm³
• LogP: 0.80360
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Chloroform, Methanol (Sparingly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 412.0785766
• Heavy Atom Count: 28
• Complexity: 624

Purity/Quality:

99% ^*data from raw suppliers

2,3,5-Tri-O-acetyl-6-chloropurine-9-β-D-ribofuranoside(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(O1)N2C=NC3=C2N=CN=C3Cl)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C2N=CN=C3Cl)OC(=O)C)OC(=O)C
• 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.

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

There total 27 articles about (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2’,3’,5’-tri-O-acetylinosine (3181-38-2) → 2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; N,N-dimethyl-aniline; trichlorophosphate; In acetonitrile; at 70 ℃; for 2h;

DOI:10.3762/bjoc.14.133

Reference yield: 100.0%

2',3',5'-tri-O-acetylinosine (3181-38-2) → 2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5)

Guidance literature:

With N,N-dimethyl-aniline; trichlorophosphate; at 115 ℃; for 0.116667h;

Reference yield: 98.0%

acetic anhydride (108-24-7) + Inosine (58-63-9) → 2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5)

Guidance literature:

With triethylamine; In acetonitrile; at 0 ℃; for 6h; Reflux;

DOI:10.1021/jm300917h

upstream raw materials:

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

2',3',5'-tri-O-acetylinosine

triacetyladenosine

6-chloro-9-trimethylsilylpurine

Downstream raw materials:

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

2',3',5'-tri-O-acetylinosine

2',3',5'-tri-O-acetylnebularine

6-Chloropurine riboside

Refernces

• 1、 Véliz, Eduardo A.,Beal, Peter A.. "C6 substitution of inosine using hexamethylphosphorous triamide in conjunction with carbon tetrahalide or N-halosuccinimide". . p. 1695 - 1697. Retrieved 2000.
• 2、 -. "Crystal form, preparation method and purpose of triacetyl-3-hydroxyphenyl adenosine". Paragraph 0006; 0036; 0038. . Retrieved 2021/06/22.
• 3、 Ciaglia, Elena,Grimaldi, Manuela,Abate, Mario,Scrima, Mario,Rodriquez, Manuela,Laezza, Chiara,Ranieri, Roberta,Pisanti, Simona,Ciuffreda, Pierangela,Manera, Clementina,Gazzerro, Patrizia,D'Ursi, Anna Maria,Bifulco, Maurizio. "The isoprenoid derivative N6-benzyladenosine CM223 exerts antitumor effects in glioma patient-derived primary cells through the mevalonate pathway". supporting information. p. 2287 - 2301. Retrieved 2017/06/28.