Inosine, 2',3',5'-triacetate

Base Information

• Chemical Name: Inosine, 2',3',5'-triacetate
• CAS No.: 3021-21-4
• Molecular Formula: C16H18 N4 O7 S
• Molecular Weight: 410.408
• European Community (EC) Number: 221-169-9
• NSC Number: 101763,98668,92028,83295,66385
• DSSTox Substance ID: DTXSID80952598
• Mol file: 3021-21-4.mol

Synonyms:3021-21-4;C16H18N4O7S;BI 293;Inosine, 6-thio-, 2',3',5'-triacetate;Oprea1_683392;DTXSID80952598;inosine, 2',3',5'-triacetate;NSC66385;NSC83295;NSC92028;NSC98668;NSC-66385;NSC-83295;NSC-92028;NSC-98668;NSC101763;AKOS003000639;NSC-101763;7687-42-5;9-(2,3,5-Tri-O-acetylpentofuranosyl)-9H-purine-6-thiol;4754-05-6

Chemical Property of Inosine, 2',3',5'-triacetate

Chemical Property:

• Melting Point: 214-216 °C
• Boiling Point: 622.3°Cat760mmHg
• PKA: 8.40±0.20(Predicted)
• Flash Point: 330.1°C
• PSA: 166.72000
• Density: 1.61g/cm³
• LogP: 0.81280
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO, Methanol
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 410.08962010
• Heavy Atom Count: 28
• Complexity: 703

Purity/Quality:

99%, ^*data from raw suppliers

6-Mercaptopurine-9-β-D-ribofuranoside2'',3'',5''-Triacetate ^*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=C2NC=NC3=S)OC(=O)C)OC(=O)C
• Uses: 2'',3'',5''-Triacetate derivative of 6-Mercaptopurine-9-β-D-ribofuranoside (M257125), a substrate for adenosine deaminase.

Technology Process of Inosine, 2',3',5'-triacetate

There total 5 articles about Inosine, 2',3',5'-triacetate 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: 81.0%

acetic anhydride (108-24-7) + 6-mercaptopurine riboside (574-25-4) → 6-thio-9-(2',3',5'-tri-O-acetyl-β-D-ribosyl)purine (3021-21-4)

Guidance literature:

molecular sieve; potassium chloride; at 100 ℃; for 3.5h;

DOI:10.1055/s-2006-958430

Reference yield:

6-Mercaptopurine (157930-09-1,157930-10-4,157930-11-5,157930-13-7,157930-14-8) + 1,2,3,5-tetraacetylribose (13035-61-5) → 6-thio-9-(2',3',5'-tri-O-acetyl-β-D-ribosyl)purine (3021-21-4)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; tin(IV) chloride; In 1,2-dichloro-ethane; at 60 ℃; for 3h; Inert atmosphere;

DOI:10.1002/chem.201003648

Reference yield:

2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5) → 6-thio-9-(2',3',5'-tri-O-acetyl-β-D-ribosyl)purine (3021-21-4)

Guidance literature:

With thiourea; In ethanol; for 1h; Heating;

DOI:10.1590/S0103-50532010000500013

upstream raw materials:

acetic anhydride

6-mercaptopurine riboside

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

6-Mercaptopurine

Downstream raw materials:

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

triacetyladenosine

6-mercaptopurine riboside

6-methyl-9-(β-D-ribofuranosyl)purine

Refernces

• 1、 Meier, Lidiane,Monteiro, Gustavo C.,Baldissera, Rodrigo A.M.,Sa?, Marcus Mandolesi. "Simple method for fast deprotection of nucleosides by triethylamine- catalyzed methanolysis of acetates in aqueous medium". body text. p. 859 - 866. Retrieved 2010/09/11.
• 2、 LEWIS,ROBINS,CHENG. "THE PREPARATION AND ANTITUMOR PROPERTIES OF ACYLATED DERIVATIVES OF". . p. 200 - 204. Retrieved 2007/10/09.