15922-23-3

Basic information

• Product Name: 2',3'-O-(isopropylidene)uridine 5'-acetate
• Synonyms: 2',3'-O-(isopropylidene)uridine 5'-acetate;2'-O,3'-O-(1-Methylethylidene)uridine 5'-acetate;2'-O,3'-O-Isopropylidene-5'-O-acetyluridine;5'-O-Acetyl-2'-O,3'-O-isopropylideneuridine;Ai3-63056;Einecs 240-061-2;Uridine, 2',3'-o-(1-methylethylidene)-, 5'-acetate
• CAS NO: 15922-23-3
• Molecular Formula: C₁₄H₁₈N₂O₇
• Molecular Weight: 326.30192
• EINECS: 240-061-2
• Mol File: 15922-23-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.328g/cm³
• PKA: 9.25±0.10(Predicted)
• CAS DataBase Reference: 2',3'-O-(isopropylidene)uridine 5'-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2',3'-O-(isopropylidene)uridine 5'-acetate(15922-23-3)
• EPA Substance Registry System: 2',3'-O-(isopropylidene)uridine 5'-acetate(15922-23-3)

Safety Data

• Hazardous Substances Data: 15922-23-3(Hazardous Substances Data)

Usage

Chemical Structure

2',3'-O-(isopropylidene)uridine 5'-acetate

Modification Description

An isopropylidene group is attached to the 2' and 3' positions of the ribose sugar, and an acetate group is attached to the 5' position of the ribose.

Purpose of Modification

Protects the nucleoside from degradation and alters its chemical properties for specific applications.

Role in RNA

Uridine is a fundamental component of RNA, crucial for protein synthesis, energy metabolism, and signal transduction.

Applications

Used in research and pharmaceuticals to manipulate the behavior and function of RNA molecules.

Upstream product

• 362-43-6 2',3'-O-isopropylideneuridine 
• 108-24-7 acetic anhydride 

Downstream Products

• 362-43-6 2',3'-O-isopropylideneuridine 
• 10212-30-3 β-D-arabinofuranosylisocytosine 
• 102935-21-7 O^5'-acetyl-O^2'-(toluene-4-sulfonyl)-uridine 
• 131-83-9 uridine 2'-monophosphate 
• 3083-77-0 araU 
• 3736-77-4 2,2'-Anhydrouridine 
• 32464-93-0 1-(2,3-O-Isopropylidene-β-D-ribofuranosyl)-3-(4-methoxybenzyl)uracil 
• 121846-03-5 1-(7,11-Anhydro-8-O-benzoyl-6,10-dideoxy-2,3-O-isopropylidene-5-O-(methoxymethyl)-D-arabino-β-D-allo-undec-10-enofuranosyl)-3-(4-methoxybenzyl)uracil 
• 121865-31-4 3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil 
• 121846-06-8 3-(4-Methoxybenzyl)-1-<(11R)-1,2,6-trideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-α-D-galacto-undecodialdo-1,5-pyrano<2,1-e><2-(benzyloxy)-4-(benzyloxycarbonyl)dihydro-Δ²-1,3,4-oxadiazinyl>-11,8-furanosyl>uracil 
• 121846-09-1 3-(4-Methoxybenzyl)-1--2,6-dideoxy-3,4:9,10-di-O-isopropylidene-7-O-(methoxymethyl)-L-allo-β-D-galacto-undecodialdo-1,5-pyranoside-11,8-furanosyl>uracil 
• 121846-07-9 3-(4-Methoxymethyl)-1-uracil 
• 121846-02-4 Benzoic acid 2-((R)-2-{(3aR,4R,6R,6aR)-6-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-2-methoxymethoxy-ethyl)-4-oxo-3,4-dihydro-2H-pyran-3-yl ester 
• 121846-05-7 1-(7,11-Anhydro-6,10-dideoxy-2,3:8,9-di-O-isopropylidene-5-O-(methoxymethyl)-D-arabino-β-D-allo-undec-10-enofuranosyl)-3-(4-methoxybenzyl)uracil 

Relevant articles and documents

Diastereoface selectivity in Radical-Mediated C-C-Bond formation of uridine 5'-Monoselenoacetals

Intramolecular radical reaction of 2',3'-O-isopropylidenuerdine 5'-monoselenoacetal 6 appeared to result in reverse stereoselectivity to that of the corresponding 5'-aldehyde (3). Intermolecular version of this reaction by using allyltribytylstannane as a radical acceptor showed preferential anti-Cram diastereoface selection.

Fe2(SO4)3·xH2O-catalyzed per-O-acetylation of sugars compatible with acid-labile protecting groups adopted in carbohydrate chemistry

Fully acetylated saccharides are inexpensive and very useful starting materials for the synthesis of many naturally occurring glycosides, oligosaccharides, and glycoconjugates. Ferric sulfate hydrate (Fe2(SO4)3·xH2O) was found to be a valuable Lewis acid promoter in the per-O-acetylation reaction of saccharides with acetic anhydride in 100% of conversion rate and 88-99% yields. Interestingly, the procedure is perfectly compatible with the presence of a variety of acid-labile protecting groups, such as isopropylidene, benzylidene, trityl, and TBDMS groups. The reactions were simply performed by stirring the mixture of a sugar with a slight excessive acetic anhydride in the presence of 2.0 mol % of Fe2(SO4)3·xH2O at rt and the pure products were obtained by a simple dilution of the reaction mixture with dichloromethane and washings with aqueous Na2CO3.

Pyridine-free and solvent-free acetylation of nucleosides promoted by molecular sieves

A practical method for the acetylation of purine and pyrimidine nucleosides employing a combination of acetic anhydride and potassium-exchanged molecular sieves is described. Besides the high yields obtained for the acylated nucleosides, the procedure is simple, inexpensive and environmentally benign, avoiding the use of pyridine or co-solvents as additives. Georg Thieme Verlag Stuttgart.