8-vinyladenosine

Base Information

• Chemical Name: 8-vinyladenosine
• CAS No.: 142386-40-1
• Molecular Formula: C₁₂H₁₅N₅O₄
• Molecular Weight: 293.282
• Mol file: 142386-40-1.mol

Synonyms:8-Vinyl Adenosine;(2R,3R,4S,5R)-2-(6-Amino-8-vinyl-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol;FEAC02;

Chemical Property of 8-vinyladenosine

Chemical Property:

• Vapor Pressure: 7.09E-20mmHg at 25°C
• Boiling Point: 688°Cat760mmHg
• Flash Point: 369.9°C
• PSA: 139.54000
• Density: 1.83g/cm³
• LogP: -0.75580

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 8-vinyladenosine

There total 6 articles about 8-vinyladenosine 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: 50.0%

8-ethenyl-2',3',5'-tris-O-(tert-butyldimethylsilyl)adenosine (132065-04-4) → 8-vinyladenosine (142386-40-1)

Guidance literature:

With ammonium fluoride; In methanol; at 60 - 70 ℃;

DOI:10.1021/jm00001a025

Reference yield:

9-((2R,3R,4R,5R)-3,4-Bis-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-8-vinyl-9H-purin-6-ylamine → 8-vinyladenosine (142386-40-1)

Guidance literature:

With ammonium chloride; In methanol; Yield given; Heating;

DOI:10.1021/jm00072a013

Reference yield:

2',3',5'-tris-O-tert-butyldimethylsilyl-8-iodoadenosine (132087-98-0) → 8-vinyladenosine (142386-40-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / (Ph₃P)4Pd / dimethylformamide / 1.5 h / 90 °C

2: 50 percent / NH₄F / methanol / 60 - 70 °C

With ammonium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00001a025

upstream raw materials:

tetravinyltin (IV)

8-bromoadenosine

8-ethenyl-2',3',5'-tris-O-(tert-butyldimethylsilyl)adenosine

2',3',5'-tris-O-tert-butyldimethylsilyl-8-iodoadenosine

Refernces

• 1、 Manfredini,Baraldi,Bazzanini,Marangoni,Simoni,Balzarini,De Clercq. "Synthesis and cytotoxic activity of 6-vinyl- and 6-ethynyluridine and 8- vinyl- and 8-ethynyladenosine". . p. 199 - 203. Retrieved 1995.