[(3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate

Base Information

• Chemical Name: [(3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate
• CAS No.: 130-49-4
• Molecular Formula: C10H14 N5 O7 P
• Molecular Weight: 347.224
• Mol file: 130-49-4.mol

Synonyms:

Chemical Property of [(3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate

Chemical Property:

• Melting Point: 183 °C
• Refractive Index: 1.9050 (estimate)
• Boiling Point: 815.5°Cat760mmHg
• PKA: pK1: 3.81(+1);pK2: 6.17(0) (25°C)
• Flash Point: 447°C
• PSA: 195.88000
• Density: 2.32g/cm³
• LogP: -1.28180
• Storage Temp.: −20°C
• Water Solubility.: 0.5g/L(15 oC)
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 347.06308480
• Heavy Atom Count: 23
• Complexity: 481

Purity/Quality:

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

Adenosine 2′-monophosphate fromyeast ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)OP(=O)(O)O)N
• Isomeric SMILES: C1=NC(=C2C(=N1)N(C=N2)C3[C@@H]([C@@H]([C@H](O3)CO)O)OP(=O)(O)O)N
• Uses: Adenosine 2′-monophosphate (2′-AMP) is a metabolite produced from hydrolysis of 2′,3′-cAMP. 2′-AMP inhibits proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. 2′-AMP is used in the synthesis of a new photoaffinity lable for the coenzyme site of porcine NADP-specific isocitrate dehydrogenase. 2′,3′-cAMP and 2′-AMP represent a new unexplored pathway for adenosine-based cell regulation.

Technology Process of [(3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate

There total 51 articles about [(3R,4R,5R)-2-(6-aminopurin-9-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] dihydrogen phosphate 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:

C10H12Cl2N5O5P (34051-17-7) → C10H15N5O15P4 (68914-00-1) + adenosine monophosphate (84-21-9) + 5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) + adenosine 2'-monophosphate (130-49-4) + 3'-phosphoadenosine-5'-phosphate (1053-73-2) + ATP (56-65-5,896506-78-8)

Guidance literature:

With tributyl-amine; bis(tri-n-butylammonium) pyrophosphate; N,N-dimethyl-formamide; In trimethyl phosphite; at 0 ℃; for 0.0166667h;

DOI:10.1080/15257771003709569

Reference yield:

adenosine (58-61-7) → adenosine monophosphate (84-21-9) + 5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) + adenosine 2',3'-cyclic monophosphate (634-01-5) + adenosine 2'-monophosphate (130-49-4)

Guidance literature:

With hydroxyapatite; ammonium ferrocyanide; water; ammonium formate; urea; at 85 ℃;

DOI:10.1002/anie.201908272

Reference yield:

adenosine (58-61-7) → C10H15N5O15P4 (68914-00-1) + adenosine monophosphate (84-21-9) + 5'-adenosine monophosphate (61-19-8,24937-83-5,67583-85-1) + adenosine 2'-monophosphate (130-49-4) + 3'-phosphoadenosine-5'-phosphate (1053-73-2) + ATP (56-65-5,896506-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: trichlorophosphate / trimethyl phosphite / 2 h / -15 °C

2: tributyl-amine; bis(tri-n-butylammonium) pyrophosphate; N,N-dimethyl-formamide / trimethyl phosphite / 0.02 h / 0 °C

With tributyl-amine; bis(tri-n-butylammonium) pyrophosphate; N,N-dimethyl-formamide; trichlorophosphate; In trimethyl phosphite;

DOI:10.1080/15257771003709569

upstream raw materials:

5'-O-(triphenylmethyl)adenosine

pyridine

dibenzyl phosphochloridate

acetic acid

Downstream raw materials:

[3']adenylic acid monobenzyl ester

adenosine monophosphate

adenosine 2',3'-cyclic monophosphate

7H-purin-6-ylamine

Refernces

• 1、 Yashiro, Morio,Higuchi, Maiko,Washizu, Yusuke,Komiyama, Makoto. "Effect of alkaline earth metal ions on the phosphodiester hydrolysis of RNA". . p. 1843 - 1844. Retrieved 2002.
• 2、 Brown et al.. "-". . p. 2708,2711. Retrieved 1952.
• 3、 Komiyama, Makoto,Kamitani, Jun,Sumaoka, Jim,Asanuma, Hiroyuki. "RNA hydrolysis by the combination of the lanthanum(III) ion and hydrogen peroxide". . p. 869 - 870. Retrieved 1996.
• 4、 Yashiro, Morio,Ishikubo, Akira,Takarada, Tohru,Komiyama, Makoto. "Lanthanide Complexes with High Stability and Efficiency for the Hydrolysis of a Ribonucleotide Dimer". . p. 665 - 666. Retrieved 1995.
• 5、 Bashkin, James K.,Jenkins, Lisa A.. "Catalytic Hydrolysis of 2',3'-Cyclic Adenosine Monophosphate by Aqua(2,2':6',2''-terpyridine)copper(II): Breakdown of the Analogy Between Activated Phosphodiesters and RNA". . p. 3631 - 3632. Retrieved 1993.
• 6、 Yashiro, Morio,Ishikubo, Akira,Komiyama, Makoto. "Preparation and Study of Dinuclear Zinc(II) Complex for the Efficient Hydrolysis of the Phosphodiester Linkage in a Diribonucleotide". . p. 1793 - 1794. Retrieved 1995.
• 7、 Schwartz. "". . p. 1393. Retrieved 1969.
• 8、 Komiyama, Makoto. "Stereospecific Cleavage of Adenosine 2',3'-Cyclic Monophosphate Catalyzed by Cyclodextrins". . p. 689 - 692. Retrieved 1988.
• 9、 Komiyama, Makoto,Sawata, Shinya,Takeshige, Yuichi. "Cooperation of cyclodextrin and alkali-metal halide for regioselective cleavage of ribonucleoside 2′,3′-cyclic phosphates". . p. 1070 - 1074. Retrieved 1992.
• 10、 Komiyama, Makoto,Matsumura, Kazunari,Matsumoto, Yoichi. "Unprecedentedly Fast Hydrolysis of the RNA Dinucleoside Monophosphates ApA and UpU by Rare Earth Metal Ions". . p. 640 - 641. Retrieved 1992.