29886-19-9

Basic information

• Product Name: 2',3'-DI-O-ACETYLADENOSINE
• Synonyms: 2',3'-DI-O-ACETYLADENOSINE;2',3'-DIACETYLADENOSINE;ADENOSINE 2',3'-DIACETATE;2'-O,3'-O-Diacetyladenosine;(2R,3R,4R,5R)-2-(2-amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diyl diacetate
• CAS NO: 29886-19-9
• Molecular Formula: C₁₄H₁₇N₅O₆
• Molecular Weight: 351.31
• EINECS: 249-929-5
• Product Categories: Nucleotides and Nucleic Acids
• Mol File: 29886-19-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 599°Cat760mmHg
• Flash Point: 316.1°C
• Appearance: /
• Density: 1.72g/cm³
• Storage Temp.: −20°C
• CAS DataBase Reference: 2',3'-DI-O-ACETYLADENOSINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-DI-O-ACETYLADENOSINE(29886-19-9)
• EPA Substance Registry System: 2',3'-DI-O-ACETYLADENOSINE(29886-19-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 29886-19-9(Hazardous Substances Data)

Usage

General Description

2',3'-DI-O-ACETYLADENOSINE is a chemical compound that belongs to the class of adenosine derivatives. It is a modified form of the nucleoside adenosine, with two acetyl groups attached to the 2' and 3' positions of the ribose sugar. 2',3'-DI-O-ACETYLADENOSINE has been studied for its potential biological activities, including anti-inflammatory and immunosuppressive properties. It has also been investigated for its potential use in cancer therapy, due to its ability to inhibit the growth of certain cancer cells. Overall, 2',3'-DI-O-ACETYLADENOSINE is a promising compound with potential therapeutic applications, particularly in the fields of inflammation, immunology, and oncology.

Upstream product

• 51600-11-4 5'-O-(p-methoxyphenyldiphenylmethyl)adenosine 
• 151928-74-4 5'-O-(4,4'-dimethoxytrityl)-2',3'-bis-O-acetyl-adenosine 
• 58-61-7 adenosine 
• 31085-55-9 (2R,3R,4S,5R)-2-(6-(tritylamino)-9H-purin-9-yl)-5-((trityloxy)methyl)tetrahydrofuran-3,4-diol 
• 7387-57-7 triacetyladenosine 
• 18048-85-6 5'-O-(triphenylmethyl)adenosine 
• 108-24-7 acetic anhydride 

Downstream Products

• 79670-88-5 adenosine 5'-triphosphate, triammonium salt 
• 56-65-5 ATP 
• 29220-54-0 adenosine 5'-<α-thio>triphosphate 
• 3256-24-4 phosphoric acid adenosin-5'-yl ester uridin-3'-yl ester 
• 22886-36-8 C₂'p5'A 
• 2382-66-3 Cytidin-(3',5')-adenosin 
• 6554-00-3 Phosphoric acid (2R,3S,4R,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl ester 
• 6918-37-2 guanylyl(2'-5')adenosine 
• 2273-76-9 adenylyl(3'-5')phosphoadenine 
• 2391-46-0 adenyl(3'-5')phophoadenine 
• 6154-31-0 AMP-Amidate 
• 61-19-8 5'-adenosine monophosphate 

Relevant articles and documents

Acetylation of nucleosides and acetyl migration.

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Synthesis and enzymic hydrolysis of acylated adenosine derivatives

Various derivatives of adenosine were prepared by acylation of adenosine (6-amino-9-(β-D-ribofuranosyl)purine (1) with different molar equivalents of acetic anhydride and/or pivaloyl chloride in pyridine. Compounds 6-acetylamino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine (3), 6-amino-9-[(2,3,5-tri-O-acetyl)-β-D-ribofuranosyl]purine (4), and 6-pivaloylamino-9-[(2,3,5-tri-O-pivaloyl)-β-D-ribofuranosyl]purine (5) were subsequently submitted to hydrolysis catalyzed by a number of hydrolytic enzymes. Regioselective enzymic deacetylation at the primary hydroxyl group of 3 and 4 with butyrylcholinesterase (BChE) produced 6-acetylamino-9-[(2,3-di-O- acetyl)-β-D-ribofuranosyl]purine (9) and 6-amino-9-[(2,3-di-O-acetyl- β-D-ribofuranosyl]purine (10), respectively. All structures were established by 1H and 13C NMR spectroscopies.

Immobilization of neutral protease from Bacillus subtilis for regioselective hydrolysis of acetylated nucleosides: Application to capecitabine synthesis

This paper describes the immobilization of the neutral protease from Bacillus subtilis and its application in the regioselective hydrolysis of acetylated nucleosides, including building blocks useful for the preparation of anticancer products. Regarding the immobilization study, different results have been obtained depending on the immobilization procedure. Epoxy hydrophobic carriers gave a poorly stable derivative that released almost 50% of the immobilized protein under the required reaction conditions. On the contrary, covalent immobilization on a differently activated hydrophilic carrier (agarose) resulted in very stable enzyme derivatives. In an attempt to explain the obtained enzyme immobilization results, the hypothetical localization of lysines on the enzyme surface was predicted in a 3D structure model of B. subtilis protease N built in silico by using the structure of Staphylococcus aureus metalloproteinase as the template. The immobilized enzyme shown a high regioselectivity in the hydrolysis of different peracetylated nucleosides. A stable enzyme derivative was obtained and successfully used in the development of efficient preparative bioprocesses for the hydrolysis of acetylated nucleosides, giving new intermediates for the synthesis of capecitabine in high yield.

Stereoselective formation of a P-P bond in the reaction of 2-alkoxy-2-thio-1,3,2-oxathiaphospholanes with O,O-dialkyl H-phosphonates and H-thiophosphonates

A new method for the formation of organohypophosphates containing a P-P bond under mild conditions, based on the DBU-assisted reaction of 2-alkoxy-2-thio-1,3,2-oxathiaphospholanes with O,O-dialkyl H-phosphonates or H-thiophosphonates, has been elaborated. The resulting triesters of P 1-thio- and P1,P2-dithiohypophosphoric acids, respectively, having O-methyl or O-ethyl groups, can be selectively dealkylated to form the corresponding di- or monoesters. Appropriately protected 2′-deoxyguanosine-3′-O-(2-thio-1,3,2-oxathiaphospholane) was converted into the corresponding P1-thio- and P1,P 2-dithiohypophosphate esters in a highly stereoselective manner (98%+ and 90%+, respectively).