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

• 18048-85-6 5'-O-(triphenylmethyl)adenosine 
• 108-24-7 acetic anhydride 
• 7387-57-7 triacetyladenosine 
• 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 
• 151928-74-4 5'-O-(4,4'-dimethoxytrityl)-2',3'-bis-O-acetyl-adenosine 
• 51600-11-4 5'-O-(p-methoxyphenyldiphenylmethyl)adenosine 

Downstream Products

• 61-19-8 5'-adenosine monophosphate 
• 6154-31-0 AMP-Amidate 
• 2391-46-0 adenyl(3'-5')phophoadenine 
• 2273-76-9 adenylyl(3'-5')phosphoadenine 
• 6918-37-2 guanylyl(2'-5')adenosine 
• 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 
• 2382-66-3 Cytidin-(3',5')-adenosin 
• 22886-36-8 C₂'p5'A 
• 3256-24-4 phosphoric acid adenosin-5'-yl ester uridin-3'-yl ester 
• 29220-54-0 adenosine 5'-<α-thio>triphosphate 
• 56-65-5 ATP 
• 79670-88-5 adenosine 5'-triphosphate, triammonium salt 

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.

Discovery of Leucyladenylate Sulfamates as Novel Leucyl-tRNA Synthetase (LRS)-Targeted Mammalian Target of Rapamycin Complex 1 (mTORC1) Inhibitors

Recent studies indicate that LRS may act as a leucine sensor for the mTORC1 pathway, potentially providing an alternative strategy to overcome rapamycin resistance in cancer treatments. In this study, we developed leucyladenylate sulfamate derivatives as LRS-targeted mTORC1 inhibitors. Compound 18 selectively inhibited LRS-mediated mTORC1 activation and exerted specific cytotoxicity against colon cancer cells with a hyperactive mTORC1, suggesting that 18 may offer a novel treatment option for human colorectal cancer.

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).