142386-40-1

Basic information

• Product Name: 8-vinyladenosine
• Synonyms: 8-vinyladenosine
• CAS NO: 142386-40-1
• Molecular Formula: C12H15 N5 O4
• Molecular Weight: 293.2786
• Mol File: 142386-40-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 688°Cat760mmHg
• Flash Point: 369.9°C
• Appearance: /
• Density: 1.83g/cm³
• Vapor Pressure: 7.09E-20mmHg at 25°C
• Refractive Index: 1.813
• CAS DataBase Reference: 8-vinyladenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-vinyladenosine(142386-40-1)
• EPA Substance Registry System: 8-vinyladenosine(142386-40-1)

Safety Data

• Hazardous Substances Data: 142386-40-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H15N5O4/c1-2-6-16-7-10(13)14-4-15-11(7)17(6)12-9(20)8(19)5(3-18)21-12/h2,4-5,8-9,12,18-20H,1,3H2,(H2,13,14,15)/t5-,8-,9-,12-/m1/s1

Upstream product

• 1112-56-7 tetravinyltin (IV) 
• 2946-39-6 8-bromoadenosine 
• 132065-04-4 8-ethenyl-2',3',5'-tris-O-(tert-butyldimethylsilyl)adenosine 
• 132087-98-0 2',3',5'-tris-O-tert-butyldimethylsilyl-8-iodoadenosine 
• 60091-08-9 8-bromo-2',3',5'-(triOTMS)adenosine 

Relevant articles and documents

Straightforward C-8 alkylation of adenosine analogues with tetraalkyltin reagents

A one step synthesis of the 8-methyl-, 8-ethyl- and 8-vinyl derivatives of adenosine, 2'-deoxyadenosine and 2',3'-dideoxyadenosine starting from the readily available 8-bromo congeners is described. This reaction makes use of a transient silylation procedure and a Pd(0) catalysed cross-coupling with tetraorganotin reagents.

Antiviral Activity of C-Alkylated Purine Nucleosides Obtained by Cross-Coupling with Tetraalkyltin Reagents

2-, 6-, And 8-alkylated (methyl, ethyl, and vinyl) adenosine analogues were synthesized by a palladium-catalyzed cross-coupling of a tetraalkyltin with the halogenated purine nucleosides.The synthesis of the 8-substituted analogues was accomplished using a transient protection procedure.The 6-alkylated-9-β-D-ribofuranosylpurines as well as 2-ethyladenosine were cytotoxic at relatively low concentrations (0.8-10 μg/mL). 8-Methyladenosine was a potent and selective inhibitor of vaccinia virus, whereas 8-ethyl- and 8-vinyladenosine were specifically inhibitory to respiratory syncytial virus. 8-Vinyladenosine displayed particular activity against herpes simplex virus (type 1).