15981-92-7

Basic information

• Product Name: 2,3'-ANHYDROTHYMIDINE
• Synonyms: 2,3'-ANHYDROTHYMIDINE;Anhydrothymidine;2,3'-Anhydro-D-thymidine;2,3'-Anhydro-1-(2'-deoxy--D-threo-pentofuranosyl)thymine;2,3'-O-Cyclothymidine;NSC 144601;O2,3'-Cyclothymidine;(2R,3R,5R)-2,3-Dihydro-3-(hydroxyMethyl)-8-Methyl-2,5-Methano-5H,9H-pyriMido[2,1-b][1,5,3]dioxazepin-9-one
• CAS NO: 15981-92-7
• Molecular Formula: C₁₀H₁₂N₂O₄
• Molecular Weight: 208.21
• Product Categories: Miscellaneous Biochemicals;5-FOA;Bases & Related Reagents;Nucleotides;Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides;Heterocycles;Intermediates
• Mol File: 15981-92-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 246-247oC
• Boiling Point: 381.8 °C at 760 mmHg
• Flash Point: 184.7 °C
• Appearance: White Powder
• Density: 1.72 g/cm³
• Storage Temp.: −20°C
• PKA: 13.97±0.10(Predicted)
• CAS DataBase Reference: 2,3'-ANHYDROTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3'-ANHYDROTHYMIDINE(15981-92-7)
• EPA Substance Registry System: 2,3'-ANHYDROTHYMIDINE(15981-92-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 15981-92-7(Hazardous Substances Data)

Usage

Chemical Properties

White Powder

Uses

An intermediate in the preparation of thymidine derivatives

Upstream product

• 2446-83-5 di-isopropyl azodicarboxylate 
• 50-89-5 thymidine 
• 357-83-5 N-(2-chloro-1,1,2-trifluoroethyl)diethylamine 
• 68-12-2 N,N-dimethyl-formamide 
• 117383-85-4 10-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methyl-8,11-dioxa-2,6-diaza-tricyclo[7.2.1.0^2,7]dodeca-3,6-dien-5-one 
• 142409-83-4 1-[(2R,4R,5S)-5-Iodomethyl-4-(4-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 142409-82-3 Methoxy-acetic acid (2S,3R,5R)-2-iodomethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 
• 34308-10-6 3'-O-mesylthymidine 
• 152039-45-7 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-p-toluenesulfonyl-β-D-erythro-pentofuranosyl)thymine 
• 139212-94-5 1-(5-O-tert-butyldiphenylsilyl-2-deoxy-3-O-methylsulfonyl-α,β-D-erythro-pentofuranosyl)thymine 
• 142409-85-6 Methoxy-acetic acid (1R,10R,11R)-4-methyl-5-oxo-8,13-dioxa-2,6-diaza-tricyclo[8.2.1.0^2,7]trideca-3,6-dien-11-yl ester 
• 70838-44-7 2,3'-anhydro-5'-O-benzoyl-2'-deoxythymidine 
• 7481-90-5 3',4'-anhydrothymidine 
• 94892-66-7 1-(2,5-dideoxy-5-iodo-β-D-threo-pentofuranosyl)thymine 

Downstream Products

• 135824-27-0 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-(phenylseleno)thymidine 
• 40615-39-2 1-((2R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)- dione 
• 854389-45-0 [(2R,3R,5R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxymethyl]-phosphonic acid monomethyl ester 
• 854389-48-3 [(2R,3R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yloxymethyl]-phosphonic acid monomethyl ester 
• 191474-13-2 5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydrothymidine 
• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 25526-93-6 alovudine 
• 16053-52-4 threothymidine 

Relevant articles and documents

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Radiosynthesis of [18F]-labelled pro-nucleotides (ProtIDes)

Phosphoramidate pro-nucleotides (ProTides) have revolutionized the field of anti-viral and anti-cancer nucleoside therapy, overcoming the major limitations of nucleoside therapies and achieving clinical and commercial success. Despite the translation of P

Synthesis, structure, and biological evaluation of C-2 sulfonamido pyrimidine nucleosides

The C-2 sulfonamido pyrimidine nucleosides were prepared by opening the 2,2′- or 2,3′-bond in anhydronucleosides under nucleophilic attack of sulfonamide anions. Reaction of the sodium salt of p-toluenesulfonamide or 2-(aminosulfonyl)-N,N-dimethylnicotinamide with 2,2′-anhydro-1-(β-D-arabinofuranosyl)cytosine gave the C-2 sulfonamido derivatives in excellent yields. Ring opening of the less reactive 2,2′-anhydrouridine and 2,3′-anhydrothymidine could be accomplished with DBU/CH3CN activation of p-toluenesulfonamide, giving moderate yields for C-2 sulfonamido derivatives. The action of acetic acid or ZnBr2/CH2Cl2 on 5-methyl-N2-tosyl-1-(2-deoxy-5-O-trityl-β-D-threo- pentofuranosyl)isocytosine led to the cleavage of both the protection group and the nucleoside bond, yielding 5-methyl-N2-tosylisocytosine as the major product. Structures of the prepared C-2 sulfonamido nucleosides were confirmed by the 1D and 2D NMR experiments, and X-ray structural analysis of 4-imino-N2-tosylamino-1-(β-D-arabinofuranosyl)pyrimidine. Both methods confirmed β-configuration and anti-conformation of the 2-sulfonamido nucleosides. The investigated compounds displayed moderate inhibition of tumor cell growth in vitro, as determined by the MTT assay using six different human tumor cell lines.