65174-96-1

Basic information

• Product Name: vidarabine 2',3'-diacetate
• Synonyms: vidarabine 2',3'-diacetate
• CAS NO: 65174-96-1
• Molecular Formula: C14H17N5O6
• Molecular Weight: 351.31468
• Mol File: 65174-96-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 599°C at 760 mmHg
• Flash Point: 316.1°C
• Appearance: /
• Density: 1.72g/cm³
• Vapor Pressure: 3.37E-15mmHg at 25°C
• Refractive Index: 1.724
• CAS DataBase Reference: vidarabine 2',3'-diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: vidarabine 2',3'-diacetate(65174-96-1)
• EPA Substance Registry System: vidarabine 2',3'-diacetate(65174-96-1)

Safety Data

• Hazardous Substances Data: 65174-96-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H17N5O6/c1-6(21)23-10-8(3-20)25-14(11(10)24-7(2)22)19-5-18-9-12(15)16-4-17-13(9)19/h4-5,8,10-11,14,20H,3H2,1-2H3,(H2,15,16,17)/t8-,10-,11+,14-/m1/s1

Upstream product

• 5536-17-4 arabinosyl adenine 
• 1040031-35-3 9-[5'-O-(tert-butyldiphenylsilyl)-β-D-arabinofuranosyl]adenine 
• 15830-52-1 (2R,3R,4S,5R)-2-(acetoxymethyl)-5-(6-amino-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate 

Downstream Products

• 65174-95-0 9-(2-O-acetyl-β-D-arabinofuranosyl)adenine 
• 65286-65-9 9-<3-O-acetyl-β-D-arabinofuranosyl>adenine 
• 74829-57-5 9-<2,5-di-O-acetyl-β-D-arabinofuranosyl>adenine 

Relevant articles and documents

Enzymatic regioselective and complete deacetylation of two arabinonucleosides

Candida antarctica lipase B (CAL-B)-catalysed regioselective deacetylation of 2′,3′,5′-tri- O-acetyl-1-β- d-arabinofuranosyluracil (1) and 2′,3′,5′-tri- O-acetyl-9-β- d-arabinofuranosyladenine (2) was studied. The choice of the reaction medium allowed the regioselective formation of products bearing different degree of acetylation: in isopropanol, CAL-B catalysed the formation of the corresponding 2′- O-acetylated arabinonucleosides, while hydrolyses afforded the 2′,3′-di- O-acetylated products. In particular, the procedure herein described allows a simple and efficient preparation of the reported vidarabine prodrug 2′,3′-di- O-acetyl-9-β- d-arabinofuranosyladenine, avoiding the utilisation of protective groups. Moreover, to achieve full deacetylation of the assayed substrates, a set of commercial hydrolases and fungal keratinases from Doratomyces microsporus (DMK) and Paecilomyces marquandii (PMK) were tested. While only PMK and DMK catalysed the quantitative complete deacetylation of 1, DMK accomplished full deacetylation of 2 in shorter time than the other assayed enzymes.

Use of 9-(beta-D-arabinofuranosyl) adenine derivatives for the preparation of pharmaceutical compositions for the treatment of aids

9-(β-D-arabinofuranosyl)adenine, also commonly known as Ara-A or vidarabine, esters thereof, or a pharmaceutically acceptable salt thereof, possess antiviral activity against the HTLV-III/LAV virus implicated in acquired immune deficiency syndrome (AIDS). The invention is related to the use of compounds of formula I for the preparation of pharmaceutical compositions useful in the treatment of infections of the HTLV-III/LAV virus in patients.

9-(3-O-Acyl-β-D-arabinofuranosyl)adenine compounds, 9-(2,3-di-O-acyl-β-D-arabinofuranosyl)-adenine compounds, and method for their production

9-(3-O-Acyl-β-D-arabinofuranosyl)adenine compounds, 9-(2,3-di-O-acyl-β-D-arabinofuranosyl)adenine compounds, and their production by reacting in each case the corresponding 5-silyl ether derivative with a tetraalkylammonium fluoride. The compounds are useful as antiviral agents. The compounds are water-soluble and lipophilic, thereby being adaptable to a wide variety of pharmaceutical formulations.