ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(2-AMINO-6-CHLORO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER

Base Information

• Chemical Name: ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(2-AMINO-6-CHLORO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER
• CAS No.: 16321-99-6
• Molecular Formula: C16H18 Cl N5 O7
• Molecular Weight: 427.801
• Hs Code.: 2933599590
• Mol file: 16321-99-6.mol

Synonyms:9H-Purine,2-amino-6-chloro-9-b-D-ribofuranosyl-, 2',3',5'-triacetate (8CI); 9H-Purine,2-amino-6-chloro-9-b-O-ribofuranosyl-, 2',3',5'-triacetate (7CI);2-Amino-6-chloro-9-(2',3',5'-tri-O-acetyl-b-D-ribofuranosyl)purine; 2-Amino-6-chloropurineribonucleoside triacetate; 2',3',5'-Tri-O-acetyl-6-chloroguanosine; NSC 70388

Chemical Property of ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(2-AMINO-6-CHLORO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER

Chemical Property:

• Vapor Pressure: 4E-16mmHg at 25°C
• Melting Point: 146.0 to 150.0 °C
• Boiling Point: 637°Cat760mmHg
• PKA: 1.69±0.10(Predicted)
• Flash Point: 339°C
• PSA: 157.75000
• Density: 1.7g/cm³
• LogP: 0.96700
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Methanol

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(2-AMINO-6-CHLORO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER

There total 15 articles about ACETIC ACID (2R,3R,4R,5R)-3,4-DIACETOXY-5-(2-AMINO-6-CHLORO-PURIN-9-YL)-TETRAHYDRO-FURAN-2-YLMETHYL ESTER 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-acetyl-guanosine (6979-94-8) → 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (16321-99-6)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; N,N-dimethyl-aniline; trichlorophosphate; at 90 ℃; for 0.166667h;

DOI:10.1016/j.carres.2017.09.010

Reference yield: 89.0%

2-Amino-6-chloropurine riboside (2004-07-1) + acetic anhydride (108-24-7) → 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (16321-99-6)

Guidance literature:

With pyridine; In N,N-dimethyl-formamide; at 80 ℃; for 2h;

DOI:10.1016/j.bmc.2004.03.031

Reference yield: 82.0%

2',3',5'-triacetylguanosine → 2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (16321-99-6)

Guidance literature:

With tetraethylammonium chloride; triethylamine; trichlorophosphate; In toluene; at 75 - 85 ℃; for 2h;

upstream raw materials:

acetic anhydride

G

2',3',5'-tri-O-acetyl-guanosine

2-Amino-6-chloropurine riboside

Downstream raw materials:

2-Amino-6-<(4-methylphenyl)thio>-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

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

2-Amino-6-chloropurine riboside

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-chloro-2-(cyclohexanecarbonyl-amino)-purin-9-yl]-tetrahydro-furan-3-yl ester

Refernces

• 1、 Story, Sherry,Gupta, Mukta,Bonsu, Eric,Nair, Vasu. "Inhibitors of inosine monophosphate dehydrogenase: Probes for antiviral drug discovery". . p. 717 - 720. Retrieved 2005.
• 2、 Collier, Alice,Wagner, Gerd K.. "Base-modified GDP-mannose derivatives and their substrate activity towards a yeast mannosyltransferase". . p. 91 - 96. Retrieved 2017.
• 3、 Camp, David,Green, Jennifer M.,Kaiser, Sonya M.,Moni, Roger W.,Townsend-Nicholson, Andrea,Schofield, Peter R.,Quinn, Ronald J.. "Diimidazo[1,2-c:4',5'-e]pyrimidines: Adenosine agonist activity demonstrated by microphysiometry". . p. 691 - 694. Retrieved 1998.
• 4、 Adah, Steven A.,Nair, Vasu. "Synthesis of complex ethynyladenosines using organic triflic enolates in palladium-atalyzed reactions: Potential agonists for the adenosine A2 receptor". . p. 6747 - 6754. Retrieved 1997.
• 5、 Tian, Miao,Chen, Ning,Xu, Fangming,Li, Xiuxiu,Li, Shunlai,Du, Hongguang. "Expedient synthesis of 2-alkylthio-N6-aryladenosines from guanosine". . p. 8 - 22. Retrieved 2018.
• 6、 Buchanan, Helena S.,Pauff, Steven M.,Kosmidis, Tilemachos D.,Taladriz-Sender, Andrea,Rutherford, Olivia I.,Hatit, Marine Z. C.,Fenner, Sabine,Watson, Allan J. B.,Burley, Glenn A.. "Modular, Step-Efficient Palladium-Catalyzed Cross-Coupling Strategy to Access C6-Heteroaryl 2-Aminopurine Ribonucleosides". . p. 3759 - 3762. Retrieved 2017.
• 7、 Kamaike,Kinoshita,Niwa,Hirose,Suzuki,Ishido. "Efficient methods for the synthesis of [2-15N]guanosine and 2′-deoxy[2-15N]guanosine derivatives". . p. 59 - 75. Retrieved 2001.
• 8、 Bhakta, Sanjib,Brucoli, Federico,Ferguson, Lindsay,Fox, Keith R.,Wells, Geoff. "Synthesis and biological evaluation of a novel C8-pyrrolobenzodiazepine (PBD) adenosine conjugate. A study on the role of the PBD ring in the biological activity of PBD-conjugates". supporting information. . Retrieved 2020/03/19.
• 9、 Debiec, Katarzyna,Matuszewski, Michal,Podskoczyj, Karolina,Leszczynska, Grazyna,Sochacka, Elzbieta. "Chemical Synthesis of Oligoribonucleotide (ASL of tRNALys T. brucei) Containing a Recently Discovered Cyclic Form of 2-Methylthio-N6-threonylcarbamoyladenosine (ms2ct6A)". supporting information. . Retrieved 2019/08/26.