3249-94-3

Basic information

• Product Name: 2,2'-ANHYDRO-1-(5'-O-TRIPHENYLMETHYL-BETA-D-ARABINOFURANOSYL)-URACIL
• Synonyms: 2,2'-ANHYDRO-1-(5'-O-TRIPHENYLMETHYL-BETA-D-ARABINOFURANOSYL)-URACIL;2,2''-ANHYDRO-1-(5''-O-TRIPHENYLMETHYL-SS-D-ARABINOFURANOSYL)-URACIL;(2S)-2,3,3aα,9aα-Tetrahydro-3α-hydroxy-2β-[(triphenylmethoxy)methyl]-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one;(2S,3aα,9aα)-2,3,3a,9a-Tetrahydro-3α-hydroxy-2β-[(triphenylmethoxy)methyl]-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one
• CAS NO: 3249-94-3
• Molecular Formula: C₂₈H₂₄N₂O₅
• Molecular Weight: 470.522
• Mol File: 3249-94-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 203-205 °C
• Boiling Point: 631.0±65.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• PKA: 12.50±0.40(Predicted)
• CAS DataBase Reference: 2,2'-ANHYDRO-1-(5'-O-TRIPHENYLMETHYL-BETA-D-ARABINOFURANOSYL)-URACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-ANHYDRO-1-(5'-O-TRIPHENYLMETHYL-BETA-D-ARABINOFURANOSYL)-URACIL(3249-94-3)
• EPA Substance Registry System: 2,2'-ANHYDRO-1-(5'-O-TRIPHENYLMETHYL-BETA-D-ARABINOFURANOSYL)-URACIL(3249-94-3)

Safety Data

• Hazardous Substances Data: 3249-94-3(Hazardous Substances Data)

Usage

General Description

2,2'-Anhydro-1-(5'-O-triphenylmethyl-beta-D-arabinofuranosyl)-uracil is a chemical compound with the molecular formula C39H32N2O5. It is a nucleoside analog with potential antiviral and antineoplastic activities. As a nucleoside analog, it interferes with the normal function of nucleosides and inhibits the replication of viral DNA or RNA. 2,2'-ANHYDRO-1-(5'-O-TRIPHENYLMETHYL-BETA-D-ARABINOFURANOSYL)-URACIL has the potential to be developed as a therapeutic agent for the treatment of viral infections and certain types of cancers. It is still under investigation in preclinical studies for its potential uses in medicine.

Upstream product

• 76-83-5 trityl chloride 
• 58-96-8 uridine 
• 3736-77-4 2,2'-Anhydrouridine 

Downstream Products

• 3736-77-4 2,2'-Anhydrouridine 
• 130860-04-7 2,2'-anhydro-1-<3-O-(phenoxythiocarbonyl)-5-O-trityl-β-D-threo-pentofuranosyl>uracil 
• 34407-66-4 1-(2-azido-2-deoxy-5-O-(triphenylmethyl)-β-L-ribofuranosyl)pyrimidine-2,4(1H,3H)-dione 
• 276870-92-9 Diazo-acetic acid (2R,3R,3aS,9aR)-6-oxo-2-trityloxymethyl-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-yl ester 
• 276870-93-0 C₃₀H₂₄N₂O₆ 
• 204688-13-1 1-((2R,3R,4S,5R)-3-Amino-4-hydroxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 130860-05-8 2,2'-anhydro-1-(3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil 
• 130860-06-9 1-(2-O-acetyl-3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)uracil 
• 130860-21-8 1-(2-O-acetyl-3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)-N⁴-acetylcytosine 
• 130860-07-0 1-(2-O-acetyl-3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)-4-(1,2,4-triazolyl)pyrimidinone 
• 130860-08-1 1-(3-deoxy-5-O-trityl-β-D-threo-pentofuranosyl)cytosine 
• 95906-49-3 1-(5'-O-triphenylmethyl-3'-deoxy-β-D-threopentofuranosyl)uracil 
• 1426142-20-2 1-{(5aR,6R,8R,8aS)-5a,6,8,8a-tetrahydro-6-[(triphenylmethoxy)methyl]-4H-furo[3,4-b][1,2,3]triazolo[1,5-d][1,4]oxazin-8-yl}pyrimidine-2,4(1H,3H)-dione 
• 1426142-26-8 4-amino-1-{(5aR,6R,8R,8aS)-5a,6,8,8a-tetrahydro-6-[(triphenylmethoxy)methyl]-4H-furo[3,4-b][1,2,3]-triazolo[1,5-d][1,4]oxazin-8-yl}pyrimidin-2(1H)-one 

Relevant articles and documents

Versatile synthesis of 2′-amino-2′-deoxyuridine derivatives with a 2′-amino group carrying linkers possessing a reactive terminal functionality

2,2′-Anhydrouridine has been successfully converted into the appropriate 2′-amino-2′-deoxyuridine derivatives in a reaction with isothiocyanates obtained from amino acids or α,ω-diaminoalkanes. The initially formed oxazolidine-2-thione ring is cleaved under basic conditions into the corresponding 2′-amino(substituted)-2′-deoxyuridine derivatives. The implemented additional terminal functionality in the substituent attached to the 2′-amino group allows further modifications with e.g., fluorophore moiety.

Uracil- and thymine-substituted thymidine and uridine derivatives

The four possible 3'-uracil-1-yl and 3'-thymin-1-yl derivatives of 3'- deoxythymidine and the four analogous derivatives of 2'-deoxyuridine have been synthesised from thymidine and uridine, respectively. Advantages of the 2-(methoxycarbonyl)vinyl group to prevent the formation of anhydronucleosides and SnCl2/PhSH/Et3N in relation to H2/Pd for the reduction of most azido groups are disclosed.

NUCLEOSIDES. XXVI. A FACILE SYNTHESIS OF 2,2' -ANHYDRO-ARABINO

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