15888-38-7

Basic information

• Product Name: 5'-ACETYL-2',3'-ISOPROPYLIDENEADENOSINE
• Synonyms: 5'-ACETYL-2',3'-ISOPROPYLIDENEADENOSINE;2',3'-O-ISOPROPYLIDENE-5'-O-ACETYLADENOSINE;2',3'-ISOPROPYLIDENEADENOSINE-5'-MONOACETATE;5-acetyl-2,3-isopropylenadenosine;5'-O-Acetyl-2',3'-O-isopropylidene-D-adenosine;2'-O,3'-O-(1-Methylethylidene)adenosine 5'-acetate;2'-O,3'-O-Isopropylidene-5'-O-acetyladenosine;2'-O,3'-O-Isopropylideneadenosine 5'-acetate
• CAS NO: 15888-38-7
• Molecular Formula: C₁₅H₁₉N₅O₅
• Molecular Weight: 349.34
• EINECS: 240-026-1
• Product Categories: Bases & Related Reagents;Nucleotides;Heterocycles
• Mol File: 15888-38-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 170-172°C
• Boiling Point: 562.2 °C at 760 mmHg
• Flash Point: 293.8 °C
• Appearance: /
• Density: 1.68 g/cm³
• Storage Temp.: -20°C
• Solubility: Chloroform (Slightly),Methanol (Slightly)
• CAS DataBase Reference: 5'-ACETYL-2',3'-ISOPROPYLIDENEADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-ACETYL-2',3'-ISOPROPYLIDENEADENOSINE(15888-38-7)
• EPA Substance Registry System: 5'-ACETYL-2',3'-ISOPROPYLIDENEADENOSINE(15888-38-7)

Safety Data

• Hazardous Substances Data: 15888-38-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 109816-78-6 N⁶,O^5'-diacetyl-O^2'_,O3'-isopropyliden-adenosine 
• 108-24-7 acetic anhydride 
• 362-75-4 2',3'-isopropylidene adenosine 
• 108-05-4 vinyl acetate 
• 103022-64-6 5'-acetyl-N⁶,N⁶-di-p-toluyl-2',3'-O-isopropylideneadenosine 

Downstream Products

• 362-75-4 2',3'-isopropylidene adenosine 
• 905580-72-5 [(3aR,4R,6R,6aR)-6-(6-benzenesulfonylamino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl acetate 
• 905581-18-2 ((3aR,4R,6R,6aR)-6-{6-[(anilinocarbonyl)amino]-9H-purin-9-yl}-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl acetate 
• 68074-34-0 O^5'-(4,4'-dimethoxy-trityl)-O^2'_,O3'-isopropylidene-adenosine 
• 105450-34-8 2',3'-O-isopropylidene-N⁶,N⁶,5'-O-tri-p-bromobenzoyladenosine p-bromobenzoic acid salt 
• 103022-63-5 5'-O-(4,4'-dimethoxytrityl)-N⁶,N⁶-di-p-toluyl-2',3'-O-isopropylideneadenosine 
• 105471-08-7 7,8-dihydro-2',3'-O-isopropylidene-N⁶,N⁶,5'-O-tri-p-bromobenzoyl-8,5'-O-cycloadenosine 
• 105450-35-9 1-(5-O-bromobenzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-cyano-5-di-p-bromobenzoylaminoimidazole 
• 103022-65-7 4-cyano-5-p-cyanobenzoylamino-1-(5-O-p-cyanobenzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)imidazole 
• 105450-36-0 5-p-bromobenzoyl-1-(5-O-p-bromobenzoyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-cyanoimidazole 
• 103062-68-6 N⁶,N⁶-di-p-toluyl-2',3'-O-isopropylideneadenosine 
• 76802-36-3 N⁶-p-toluoyl-2',3'-O-isopropylideneadenosine 
• 105471-07-6 4-cyano-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-5-(p-cyano-benzoylamino)imidazole 
• 93135-68-3 7,8-dihydro-2',3'-O-isopropylidene-N⁶,N⁶,7-tris(p-cyanobenzoyl)-8,5'-O-cycloadenosine 

Relevant articles and documents

Deamination of 5′-substituted-2′,3′-isopropylidene adenosine derivatives catalyzed by adenosine deaminase (ADA, EC 3.5.4.4) and complementary enzymatic biotransformations catalyzed by adenylate deaminase (AMPDA, EC 3.5.4.6): A viable route for the preparation of 5′-substituted inosine derivatives

Adenosine deaminase (ADA) catalyzes the deamination of 2′,3′-isopropylidene adenosine and the corresponding 5′-amino derivative in a 3% dimethylsulfoxide aqueous solution. Whereas ADA is unable to convert other 5′-substituted derivatives (acetate, acetamido, azide), the enzyme adenylate deaminase (AMPDA) accepts all the above compounds as substrates for their biotransformation to the corresponding 5′-substituted inosine derivatives.

Chemoselective N-Deacetylation of Protected Nucleosides and Nucleotides Promoted by Schwartz's Reagent

Protection and deprotection strategies involving the N-acetyl group are widely utilized in nucleoside and nucleotide chemistry. Herein, we present a mild and selective N-deacetylation methodology, applicable to purine and pyrimidine nucleosides, by means of Schwartz's reagent, compatible with most of the common protecting groups used in nucleoside chemistry.

Acyl migration from N6 to N7 of a 2',3'-O-isopropylideneadenosine derivative accompained by cyclonucleoside formation

Reaction of 2',3'-O-isopropylideneadenosine (1) with p-NCC6H4COCl in 1:6 Et3N-CH2Cl2 afforded the cyanoimidazole nucleoside 8 (53percent) and the 8,5'-O-cycloadenosine derivative 7 (29percent).Treatment of N6,N6-di-p-toluyl-2',3'-O-isopropilideneadenosine (23) with ZnBr2 in p-dioxane resulted in acyl migration from N6 to N7 to give the cycloadenosine derivative 4.The coordination site of the zinc cation on the base moiety of adenosine derivatives was determined by 15N nmr spectra.