5-(6-Aminopurin-9-yl)-2-methyl-3-oxolanol

Base Information

• Chemical Name: 5-(6-Aminopurin-9-yl)-2-methyl-3-oxolanol
• CAS No.: 6698-26-6
• Molecular Formula: C10H13N5O2
• Molecular Weight: 235.246
• Hs Code.: 29349990
• NSC Number: 95943,95107
• DSSTox Substance ID: DTXSID90927095
• Wikidata: Q27165549
• Mol file: 6698-26-6.mol

Synonyms:5-(6-aminopurin-9-yl)-2-methyl-3-oxolanol;5-(6-aminopurin-9-yl)-2-methyloxolan-3-ol;5-(6-AMINOPURIN-9-YL)-2-METHYLTETRAHYDROFURAN-3-OL;13116-42-2;NSC-95943;9-(2,5-dideoxypentofuranosyl)-9h-purin-6-amine;NSC95107;CHEMBL282503;SCHEMBL23396436;CHEBI:93820;DTXSID90927095;NSC95943;BDBM50140057;NSC-95107;AKOS032947862;PD069187;FT-0636240;BRD-A20131130-001-01-7;Q27165549;5-(6-Amino-purin-9-yl)-2-methyl-tetrahydro-furan-3-ol;2-Hydroxymethyl-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3,4-diol5-(6-Amino-purin-9-yl)-2-methyl-tetrahydro-furan-3-ol

Chemical Property of 5-(6-Aminopurin-9-yl)-2-methyl-3-oxolanol

Chemical Property:

• Appearance/Colour: White Solid
• Boiling Point: 547 °C at 760 mmHg
• PKA: 14.06±0.60(Predicted)
• Flash Point: 284.6 °C
• PSA: 99.08000
• Density: 1.77 g/cm³
• LogP: 0.65800
• Storage Temp.: 0-6°C
• Solubility.: DMSO: soluble
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 235.10692467
• Heavy Atom Count: 17
• Complexity: 292

Purity/Quality:

99% ^*data from raw suppliers

2?,5?-Dideoxyadenosine ≥95% (HPLC), solid ^*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: CC1C(CC(O1)N2C=NC3=C(N=CN=C32)N)O
• General Description: 2',5'-Dideoxyadenosine (also known as NSC 95943) is a nucleoside analog investigated for its role in inhibiting adenylyl cyclase through interactions at the enzyme's "P"-site. It serves as a scaffold for synthesizing affinity probes due to its structural compatibility with 3'-substitutions, enabling the development of analogs like iodo-aryl-azido derivatives. These modifications aim to explore adenylyl cyclase inhibition and elucidate the enzyme's functional domains, though synthetic challenges such as poor coupling efficiency and solubility were noted. The resulting analogs, particularly nitro-substituted variants, demonstrated inhibitory potency, highlighting their potential as tools for studying adenylyl cyclase isozymes. Further research is needed to refine these probes for covalent targeting applications.

Technology Process of 5-(6-Aminopurin-9-yl)-2-methyl-3-oxolanol

There total 3 articles about 5-(6-Aminopurin-9-yl)-2-methyl-3-oxolanol 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: 72.0%

(2S,3S,5R)-5-(6-Amino-purin-9-yl)-2-phenylsulfanylmethyl-tetrahydro-furan-3-ol (108906-82-7) → 2' 5'-dideoxyadenosine (6698-26-6)

Guidance literature:

With nickel; In methanol; isopropyl alcohol; for 48h; Heating;

DOI:10.1080/15257779508010705

Reference yield:

2'-deoxy-D-adenosine (958-09-8,7005-15-4) → 2' 5'-dideoxyadenosine (6698-26-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / Bu₃P / pyridine / 12 h / Ambient temperature

2: 72 percent / Raney Ni / methanol; propan-2-ol / 48 h / Heating

With tributylphosphine; nickel; In pyridine; methanol; isopropyl alcohol;

DOI:10.1080/15257779508010705

Reference yield:

→ 2' 5'-dideoxyadenosine (6698-26-6)

Guidance literature:

DOI:10.1021/bi00865a029

upstream raw materials:

(2S,3S,5R)-5-(6-Amino-purin-9-yl)-2-phenylsulfanylmethyl-tetrahydro-furan-3-ol

2'-deoxy-D-adenosine

Downstream raw materials:

2-deoxy-D-ribose

7H-purin-6-ylamine

C₄₃H₆₁N₆O₇P

Phosphoric acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-methyl-tetrahydro-furan-3-yl ester 2-[(5-dimethylamino-naphthalene-1-sulfonyl)-methyl-amino]-ethyl ester 4-nitro-phenyl ester

Refernces

Synthesis of iodo-aryl-azido adenosine analogs as affinity ligands for adenylyl cyclase

10.1080/15257779408010676

The research aimed to develop potential affinity probes for adenylyl cyclase by synthesizing a series of 3'-substituted 2',5'-dideoxyadenosine analogs. The study focused on leveraging the enzyme's sensitivity to "P"-site-mediated inhibition and its tolerance for large 3'-ribose substitutions. The researchers encountered challenges with traditional synthesis methods due to poor coupling efficiencies and solubility issues with 2',5'-dideoxyadenosine. To address these, they developed an alternative approach involving the formation of symmetric aryl anhydrides, which were then coupled to 2',5'-dideoxyadenosine using base-catalyzed esterification. Key chemicals used in the research included 2',5'-dideoxyadenosine, various aryl acids (such as (4-nitrophenyl)-acetic acid and (4-azido-3-iodophenyl)-acetic acid), and coupling agents like DCC (dicyclohexylcarbodiimide) and DMAP (4-dimethylaminopyridine). The synthesized compounds were tested for their ability to inhibit adenylyl cyclase, with the nitro-analogs showing higher potency than the azido-iodo analogs. The study concluded that these analogs could serve as useful tools for studying the structure-function relationships of adenylyl cyclase, particularly in elucidating the characteristics of the "P"-site domain across different isozymes. Future work is suggested to further explore and identify additional covalent affinity ligands for adenylyl cyclase.