6-Chloropurine riboside

Base Information

• Chemical Name: 6-Chloropurine riboside
• CAS No.: 2004-06-0
• Molecular Formula: C10H11ClN4O4
• Molecular Weight: 286.675
• Hs Code.: 29389090
• Mol file: 2004-06-0.mol

Synonyms:6-Chloropurineribonucleoside;6-chloro-9-(β-D-ribofuranosyl)-9H-purine;(2R,3R,4S,5R)-2-(6-Chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydro-3,4-furandiol;6-Chloro-9-(β-D-ribofuranosyl)-9H-purine;9H-purine, 6-chloro-9-(β-d-ribofuranosyl)-;

Chemical Property of 6-Chloropurine riboside

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 158-162 °C (dec.)(lit.)
• Refractive Index: -45 ° (C=0.8, H2O)
• Boiling Point: 614.8 °C at 760 mmHg
• PKA: 13.06±0.70(Predicted)
• Flash Point: 325.6 °C
• PSA: 122.75000
• Density: 2.03 g/cm³
• LogP: -1.65270
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

6-Chloro-6-deoxyinosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: 6-CHLOROPURINE RIBOSIDE acts as a reactant in the synthesis of isozyme-specific enzyme inhibitors as well as in the preparation of dog coronary artery receptor agonists.

Technology Process of 6-Chloropurine riboside

There total 29 articles about 6-Chloropurine 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: 100.0%

2',3',5'-O-triacetyl-6-chloroinosine (5987-73-5) → 6-Chloropurine riboside (2004-06-0)

Guidance literature:

With ammonia; In methanol; at -20 - 0 ℃;

DOI:10.1016/j.bmcl.2009.09.112

Reference yield: 93.0%

C30H27ClN4O5 → 6-Chloropurine riboside (2004-06-0)

Guidance literature:

With hydrogenchloride; In water; acetonitrile; at 20 ℃; for 0.25h; pH=Ca. 1; Inert atmosphere;

DOI:10.1021/acs.orglett.5b02332

Reference yield: 91.0%

1,2,3,5-tetra-O-acetyl-D-ribofuranose (28708-32-9) + 6-chloro-7H-purine (87-42-3,111055-92-6) → 6-Chloropurine riboside (2004-06-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 60 ℃; for 2h;

DOI:10.1021/jm401497a

upstream raw materials:

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate

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

2,3,5-tri-O-acetyl-α-D-ribofuranosyl chloride

Inosine

Downstream raw materials:

6-(1-pyrrolidinyl)-9-(β-D-ribofuranosyl)purine

(2R,3S,4R,5R)-2-Hydroxymethyl-5-[6-(2-thiophen-3-yl-ethylamino)-purin-9-yl]-tetrahydro-furan-3,4-diol

N⁶-(2,6-dichloro-benzyl)-adenosine

(2R,3R,4S,5R)-2-{6-[2-(2-Chloro-phenyl)-ethylamino]-purin-9-yl}-5-hydroxymethyl-tetrahydro-furan-3,4-diol

Refernces

• 1、 Zhao,Pagano,Wang,Shallop,Gaffney,Jones. "Use of a 13C atom to differentiate two 15N-labeled nucleosides". . p. 7832 - 7835. Retrieved 1997.
• 2、 Robins. "". . p. 2654. Retrieved 1960.
• 3、 Del Arco, Jon,Mills, Alberto,Gago, Federico,Fernández-Lucas, Jesús. "Structure-Guided Tuning of a Selectivity Switch towards Ribonucleosides in Trypanosoma brucei Purine Nucleoside 2′-Deoxyribosyltransferase". . p. 2996 - 3000. Retrieved 2019/11/11.