2-Octynyladenosine

Base Information

• Chemical Name: 2-Octynyladenosine
• CAS No.: 90596-75-1
• Molecular Formula: C₁₈H₂₅N₅O₄
• Molecular Weight: 375.428
• DSSTox Substance ID: DTXSID10238211
• Nikkaji Number: J379.786D
• Wikidata: Q83120474
• Pharos Ligand ID: YGCNA23W2YTW
• ChEMBL ID: CHEMBL2113496
• Mol file: 90596-75-1.mol

Synonyms:2-(1-octynyl)adenosine;2-O-Ado;2-octynyladenosine;YT 146;YT-146

Chemical Property of 2-Octynyladenosine

Chemical Property:

• Vapor Pressure: 4.65E-21mmHg at 25°C
• Boiling Point: 708.3°Cat760mmHg
• Flash Point: 382.2°C
• PSA: 139.54000
• Density: 1.46g/cm³
• LogP: 0.92310
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 375.19065430
• Heavy Atom Count: 27
• Complexity: 552

Purity/Quality:

2-(1-OCTYNYL)ADENOSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC#CC1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)CO)O)O)N
• Isomeric SMILES: CCCCCCC#CC1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N

Technology Process of 2-Octynyladenosine

There total 6 articles about 2-Octynyladenosine 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: 90.0%

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-chloro-2-oct-1-ynyl-purin-9-yl)-tetrahydro-furan-3-yl ester (133560-14-2) → YT-146 (90596-75-1)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; at 70 ℃; for 20h;

DOI:10.1021/jm00090a017

Reference yield: 84.0%

n-octyne (629-05-0) + 2-iodoadenosine (35109-88-7) → YT-146 (90596-75-1)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 80 ℃; for 1h;

DOI:10.1021/jm00080a007

Reference yield:

6-chloro-2-iodo-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine (5987-76-8) → YT-146 (90596-75-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / CuI, (PPh₃)2PdCl₂, Et₃N / dioxane / 2 h / Ambient temperature

2: 90 percent / conc. NH₄OH / dioxane / 20 h / 70 °C

With bis-triphenylphosphine-palladium(II) chloride; ammonium hydroxide; copper(l) iodide; triethylamine; In 1,4-dioxane;

DOI:10.1021/jm00090a017

upstream raw materials:

n-octyne

2-iodoadenosine

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-chloro-2-oct-1-ynyl-purin-9-yl)-tetrahydro-furan-3-yl ester

6-chloro-2-iodo-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine