2,6-Dichloropurine riboside

Base Information

• Chemical Name: 2,6-Dichloropurine riboside
• CAS No.: 13276-52-3
• Molecular Formula: C10H10Cl2N4O4
• Molecular Weight: 321.12
• Hs Code.: 2934999090
• Mol file: 13276-52-3.mol

Synonyms:2,6-Dichloropurine riboside; (2R,3R,4S,5R)-2-(2,6-Dichloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol;

Chemical Property of 2,6-Dichloropurine riboside

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 9.86E-15mmHg at 25°C
• Melting Point: >190°C (dec)
• Refractive Index: 1.854
• Boiling Point: 589.3 °C at 760 mmHg
• PKA: 13.00±0.70(Predicted)
• Flash Point: 310.2 °C
• PSA: 113.52000
• Density: 2.14 g/cm³
• LogP: -0.25540
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water

Purity/Quality:

98%, ^*data from raw suppliers

2,6-Dichloropurine-9-β-D-riboside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,6-Dichloropurine-9-β-D-riboside is a useful reagent for the design of AB680 as potent and selective inhibitor of CD73.

Technology Process of 2,6-Dichloropurine riboside

There total 11 articles about 2,6-Dichloropurine riboside 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: 85.0%

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate (3056-18-6) → 2,6-dichloropurine riboside (13276-52-3)

Guidance literature:

With acetyl chloride; In methanol; at 0 - 10 ℃; for 1.5h; Inert atmosphere;

Reference yield: 82.0%

6-Chloro-2-nitro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine (266360-68-3) → 2,6-dichloropurine riboside (13276-52-3)

Guidance literature:

With hydrogenchloride; In ethanol; at 20 ℃; for 10h;

Reference yield: 82.0%

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate (15373-23-6,339091-08-6) → 2,6-dichloropurine riboside (13276-52-3)

Guidance literature:

With acetyl chloride; In methanol; at 0 - 10 ℃; for 4h; Inert atmosphere;

upstream raw materials:

2,6 dichloropurine

uridine

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

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate

Downstream raw materials:

2-Amino-6-chloropurine riboside

6-cyclopropylamino-2-chloro-9-(β-D-ribofuranosyl)purine

(2R,3R,4S,5R)-2-(6-(benzylamino)-2-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

2-hydrazinoadenosine

Refernces

• 1、 Zhang, Min,Fan, Shiyong,Zhou, Xinbo,Xie, Fei,Li, Song,Zhong, Wu. "Design, synthesis and biological evaluation of 2-hydrazinyladenosine derivatives as A2A adenosine receptor ligands". . p. 310 - 324. Retrieved 2019.
• 2、 Giessmann, Robert T.,Kaspar, Felix,Klare, Hendrik F. T.,Kurreck, Jens,Neubauer, Peter,Paulick, Katharina,R?hrs, Viola,Wagner, Anke,Westarp, Sarah,Yehia, Heba. "Efficient biocatalytic synthesis of dihalogenated purine nucleoside analogues applying thermodynamic calculations". . . Retrieved 2020/02/28.