77421-68-2

Basic information

• Product Name: [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate
• Synonyms: 2,4(1H,3H)-pyrimidinedione, 1-[(2R,5S)-5-[(acetyloxy)methyl]-2,5-dihydro-2-furanyl]-5-methyl-; Thymidine, 2',3'-didehydro-3'-deoxy-, 5'-acetate
• CAS NO: 77421-68-2
• Molecular Formula: C₁₂H₁₄N₂O₅
• Molecular Weight: 266.25
• Mol File: 77421-68-2.mol
• Article Data: 11

Chemical Properties

• Density: 1.317g/cm³
• Refractive Index: 1.539
• CAS DataBase Reference: [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate(77421-68-2)
• EPA Substance Registry System: [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate(77421-68-2)

Safety Data

• Hazardous Substances Data: 77421-68-2(Hazardous Substances Data)

Usage

Description

[(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate is a nucleoside thymidine derivative featuring a furan ring attached to a modified thymine base, with an additional acetate group on the furan ring. [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate is known for its unique structure and potential reactivity, making it a significant intermediate in pharmaceutical production and chemical research.

Uses

Used in Pharmaceutical Synthesis:
[(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate is used as an intermediate in the synthesis of nucleoside analogs for its potential applications in antiviral and anticancer drug development. Its unique structure allows for the creation of novel compounds with therapeutic properties.
Used in Chemical Research:
In the field of chemical research, [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate serves as a valuable compound for studying the properties and reactions of nucleoside derivatives. Its potential reactivity contributes to the advancement of knowledge in chemical synthesis and the development of new methodologies.
Used in Antiviral Applications:
[(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate is used as a key component in the development of antiviral drugs, targeting the replication and life cycle of viruses. Its incorporation into nucleoside analogs can lead to the creation of effective antiviral agents.
Used in Anticancer Applications:
In the field of oncology, [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate is utilized in the synthesis of anticancer drugs. Its potential to be incorporated into nucleoside analogs allows for the development of compounds that can target and inhibit cancer cell growth.
Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic outcomes of nucleoside analogs derived from [(2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dihydrofuran-2-yl]methyl acetate, various drug delivery systems are being developed. These systems aim to improve the compound's delivery to target cells, increasing its efficacy in treating viral and cancerous conditions.

Upstream product

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• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 3444-09-5 1,3-bis(trimethylsilyl)thymine 
• 143422-74-6 ((2R,3S)-5-Methoxy-3-phenylselanyl-tetrahydro-furan-2-yl)-methanol 
• 132747-40-1 (2R,3R)-3-(2,2-Dimethoxyethyl)oxiranemethanol 
• 143422-80-4 5'-acetyl-3'-selenophenylthymidine 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 
• 75-36-5 acetyl chloride 
• 3056-17-5 stavudin 
• 110483-43-7 1-(3,5-di-O-acetyl-2-bromo-2-deoxy-β-D-ribofuranosyl)thymine 
• 108-24-7 acetic anhydride 
• 143422-82-6 Acetic acid (2R,3S)-5-methoxy-3-phenylselanyl-tetrahydro-furan-2-ylmethyl ester 
• 143422-72-4 (2R,3S)-5,5-Dimethoxy-3-phenylselanyl-pentane-1,2-diol 

Downstream Products

• 134767-53-6 Octanoic acid (2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester 
• 3056-17-5 1-(2,3-dideoxy-D-glycero-pent-2-enofuranosyl)thymine 
• 3056-17-5 stavudin 

Relevant articles and documents

Nasal absorption of 2',3'-didehydro-3'-deoxythymidine (D4T) and its esters in rats

Nasal absorption of 2',3'-didehydro-3'-deoxythymidine (D4T) and its esters (5'-acetyl D4T: C2-D4T and 5'-hemisuccinyl D4T: Suc-D4T) was investigated in rats. Bioavailability of D4T following intranasal (i.n.) administration was 98.0%, and the elimination from plasma was as rapid as that following intravenous administration of D4T. There seemed to be complete and rapid absorption of D4T from the nasal cavity. The plasma concentration- time profile of D4T following i.n. administration of C2-D4T was almost the same as that after administration of D4T itself. This suggests that C2-D4T was rapidly absorbed from the nasal cavity, and that some amount of dosing C2-D4T was hydrolyzed to D4T before entering the systemic circulation. In contrast, Suc-D4T showed slower absorption in the i.n. administration, and the plasma D4T level was maintained for a long period.

Process for preparing 5′-acetylstavudine

The present invention relates to a process for preparing 5′-acetylstavudine, an intermediate which is useful in the preparation of 2′,3′-didehydro-3′-deoxythymidine, an active principle with antiviral action which is commonly known as stavudine (D4T).

Direct Transport of 2',3'-Didehydro-3'-deoxythymidine (D4T) and Its Ester Derivatives to the Cerebrospinal Fluid via the Nasal Mucous Membrane in Rats

We investigated the absorption and transport of 2',3'-didehydro-3'-deoxythymidine (D4T) and its ester prodrugs from the nasal cavity in rats. The absorption of D4T and its acetate (C2-D4T) was rapid and almost complete, although the hemi-succinate (Suc-D4T) was absorbed rather slowly; the plasma concentrations of the prodrug, Suc-D4T, and regenerated D4T remained unchanged throughout the experimental period (180 min). Concentrations in the cerebrospinal fluid (CSF) following intravenous (i.v.) and intranasal (i.n.) administration were also measured. After i.n. administration, drug concentrations were higher in the fraction derived from the subarachnoid space located close to the nasal mucosa than those in the fractions located far from the nasal cavity. This difference was not found following the i.v. administration of the drugs. Following nasal administration, the intact Suc-D4T was found in the CSF at a concentration higher than that of D4T, although transport of the intact prodrug to the CSF was not observed following i.v. adinistration. These results suggest that direct transport of the drugs from the nasal cavity to the CSF significantly contributes to the higher concentrations in CSF of D4T and/or its ester prodrugs, and indicate the possible value of nasal administration for the treatment of patients with AIDS dementia.