2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Base Information

• Chemical Name: 2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS No.: 3080-29-3
• Molecular Formula: C₁₀H₁₃N₅O₄
• Molecular Weight: 267.244
• NSC Number: 627048,404241,91041,247519,87676,80832,70422,7652,7359
• Wikidata: Q27165666
• ChEMBL ID: CHEMBL11909
• Mol file: 3080-29-3.mol

Synonyms:9 beta-D-xylofuranosyladenine;9 beta-D-xylosyladenine;9-xylosyladenine;9-xylosyladenine, ((9alpha)-(L))-isomer;xyloA;xylosyladenosine

Chemical Property of 2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

Chemical Property:

• Melting Point: 257.0-257.5oC (0.4 H2O)
• Boiling Point: 676.271 °C at 760 mmHg
• PKA: 13.11±0.70(Predicted)
• Flash Point: 362.796 °C
• PSA: 139.54000
• Density: 2.085 g/cm³
• LogP: -1.39880
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 267.09675391
• Heavy Atom Count: 19
• Complexity: 335

Purity/Quality:

97%min ^*data from raw suppliers

L-Adenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
• Uses: L-Adenosine is an intermediate in the synthesis of (2S,3S,4R,5R)-2-(6-Amino-9H-purin-9-yl)-5-(((3-aminophenyl)thio)methyl)tetrahydrofuran-3,4-diol (A609900), an enantiomer of (2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-(((3-aminophenyl)thio)methyl)tetrahydrofuran-3,4-diol (A577286), which an intermediate used in the synthesis of S-adenosylhomocysteine analogs with biological activities.

Technology Process of 2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

There total 3 articles about 2-(6-Aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol 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:

adenosine (58-61-7) → adenosine radical cation (58-61-7,524-69-6,2006-02-2,2946-52-3,3080-29-3,3228-71-5,4005-33-8,4185-03-9,5536-17-4,5682-20-2,5682-25-7,16136-63-3,21138-43-2,23289-16-9,28361-05-9,34512-24-8,36655-01-3,59121-72-1,59121-73-2,62560-97-8,63267-73-2,95188-52-6,142796-17-6)

Guidance literature:

With sodium chloride; In water; at 20 ℃; Quantum yield; Irradiation;

Reference yield:

→ 9-β-DL-Ribofuranosyl-adenin (58-61-7,524-69-6,2006-02-2,2946-52-3,3080-29-3,3228-71-5,4005-33-8,4185-03-9,5536-17-4,5682-20-2,5682-25-7,16136-63-3,21138-43-2,23289-16-9,28361-05-9,34512-24-8,36655-01-3,59121-72-1,59121-73-2,62560-97-8,63267-73-2,95188-52-6,142796-17-6)

Guidance literature:

9-Chlormercuri-6-benzamino-purin, 1. 2.3.5-Tri-O-benzoyl-DL-ribofuranosylchlorid <140grad>, 2. NaOH, NaOMe;

DOI:10.1248/cpb.13.616

Reference yield:

→ 1-(6-amino-purin-9-yl)-ξ-D-1-deoxy-xylofuranose (58-61-7,524-69-6,2006-02-2,2946-52-3,3080-29-3,3228-71-5,4005-33-8,4185-03-9,5536-17-4,5682-20-2,5682-25-7,16136-63-3,21138-43-2,23289-16-9,28361-05-9,34512-24-8,36655-01-3,59121-72-1,59121-73-2,62560-97-8,63267-73-2,95188-52-6,142796-17-6)

Guidance literature:

Benzamido-9-(2,3,5-tri-O-acetyl-D-xylofuranosyl)-purin (III), NaOCH3;

upstream raw materials:

adenosine

Downstream raw materials:

2',3'-O-(o,o'-biphenylmethylene)adenosine

Refernces

• 1、 Candeias,Steenken. "Ionization of purine nucleosides and nucleotides and their components by 193-nm laser photolysis in aqueous solution: Model studies for oxidative damage of DNA 1". . p. 699 - 704. Retrieved 2007/10/02.
• 2、 Shimizu,Asai,Hieda,Miyaki,Okazaki. "Preparation of L-beta-ribonucleosides and L-beta-ribonucleotides.". . p. 616 - 618. Retrieved 2007/10/04.