65174-95-0

Upstream product

• 65174-96-1 9-<2,3-di-O-acetyl-β-D-arabinofuranosyl>adenine 
• 74829-57-5 9-<2,5-di-O-acetyl-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 
• 88121-23-7 Acetic acid (2R,3S,3aR,9aR)-2-(6-amino-purin-9-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester 
• 69304-45-6 3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine 
• 88121-20-4 3′,5′-O-(1,1,3,3-tetraisopropyldisiloxyl)-2′-O-(trifluormethylsulfonyl)adenosine 
• 127-08-2 potassium acetate 
• 132887-08-2 O^2'-(4-nitro-benzenesulfonyl)-adenosine 
• 127-09-3 sodium acetate 
• 546-89-4 lithium acetate 
• 58-61-7 adenosine 
• 5536-17-4 arabinosyl adenine 
• 82870-42-6 9-<3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>adenine 
• 87970-03-4 9-<2-O-acetyl-3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>adenine 

Downstream Products

• 5536-17-4 arabinosyl adenine 

Relevant academic research and scientific papers

A method for synthesizing arabinosyladenosine (by machine translation)

The invention discloses a method for synthesizing arabinosyladenosine method, which belongs to the field of nucleoside in organic chemistry synthesis. The reaction steps are as follows: in order to adenosine as raw material, in a catalytic amount of dibutyl tin oxide or borate and under the action of the nitrobenzene sulfonyl chloride reaction, to obtain the 2 '- to the nitrobenzene sulfonyl protecting adenosine, then under the action of the potassium acetate and catalyst, undergo the substitution reaction to obtain the 2' - acetyl arabinosyladenosine, finally ammonolysis to obtain arabinosyladenosine. The synthesis method cheap raw materials, the step is short, easy to industrial production, with the actual application prospect. (by machine translation)

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.

Facile access to 2′-O-acyl prodrugs of 1- (β-D-arabinofuranosyl)-5(E)-(2-bromovinyl)uracil (BVAraU) via regioselective esterase-catalyzed hydrolysis of 2′ 3′, 5′-triesters

Treatment of 1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl) -5-[2-(trimethylsilyl)-vinyl]uracil (3) with pyridinium bromide perbromide and deacetylation gave BVAraU (2). Pig liver esterase (EC 3.1.1.1) catalysed the regioselective hydrolysis of 1-

Hydrolysis and solvent-dependent 2'→5' and 3'→5' acyl migration in prodrugs of 9-β-D-arabinofuranosyladenine

As a prerequisite to quantitative in vivo studies to further explore the promising topical activity of the 2',3'-di-O-acetyl derivative of 9-β-D-arabinofuranosyladenine (ara-A) against herpes virus infections, the kinetics of solution degradation of the 2',3'-di-O-acetyl derivative and the 2'-, 3'-, and 5'-monoacetates were investigated. The rates of aqueous solution hydrolysis were found to be consistent with rank order predictions based on a consideration of substituent effects. Preliminary in vivo hydrolysis data, however, do not correlate with such predictions, indicating a need for more systematic studies of the effect of molecular structure on enzyme-catalyzed hydrolysis. An important reaction of the 2',3'-diester and the 3'-monoester in aqueous solution, in addition to ester hydrolysis, is 3'→5' acyl migration. 2'→5' Acyl migration does not occur in water but is the predominant migration pathway in organic solvents, as verified by studies in acetonitrile. 1H NMR spectroscopy was employed to study the dependence of the conformation of the sugar ring on the solvent environment. Although a change in the equilibrium between the C(2')endo and C(3')endo conformational states does occur, it is not a dramatic change and cannot explain the solvent selectivity observed in the acyl migration kinetics.

Synthesis and evaluation of a series of 2'-O-acyl derivatives of 9-β-D-arabinofuranosyladenine as antiherpes agents

A series of four 9-(2-O-acyl-β-D-arabinofuranosyl)adenines was synthesized by acylation of 9-[3,5-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]adenine followed by removal of the tert-butyldimethylsilyl groups under conditions (HOAc, teta-N-butyammonium fluoride) that prevented acyl migration. The four 2'-O-acyl derivatives showed activity in vitro against herpes type 1 viruses [virus ratings = 1.5-2.6; MIC50 = 26-72 μg/mL (8.48-21.3 x 10-5 M)]. The 2'-O-acetyl (5a) and 2'-O-valeryl derivatives were evaluated in a guinea pig model for genital herpes (herpes type 2); only 5a showed potent activity when given 6 or 24 h postinfection.