25442-42-6

Basic information

• Product Name: 5-O-Triphenylmethyl-2-deoxy-2,3-didehyrothymidine
• Synonyms: 5-O-Triphenylmethyl-2-deoxy-2,3-didehyrothymidine;5-O-TRITYL-2',3'-ANHYDROTHYMIDINE;2,3-dihydro-8-methyl-3-[(trityloxy)methyl]-2,5-methano-5h,9h-pyrimido[2,1-b][1,5,3]dioxazepin-9-one;2,3'-Anhydro-1-(2-deoxy-5-O-trityl-b-D-threo-pentofuranosyl)-thymine;5'-Trityl-2'-deoxy-2,3'-didehydrothymidine;5'-o-Triphenylmethyl-2-deoxy-2',3-didehydrothymidine;5''-O-TRITYL-2,3''-ANHYDROTHYMIDINE (5-OTT+1);(2R,3R,5R)-2,3-Dihydro-8-methyl-3-[(triphenylmethoxy)methyl]-2,5-methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one
• CAS NO: 25442-42-6
• Molecular Formula: C₂₉H₂₆N₂O₄
• Molecular Weight: 466.53
• EINECS: 1312995-182-4
• Product Categories: Bases & Related Reagents;Nucleotides
• Mol File: 25442-42-6.mol

Chemical Properties

• Melting Point: 229-230 °C
• Boiling Point: 595.742 °C at 760 mmHg
• Flash Point: 314.094 °C
• Appearance: White solid
• Density: 1.28 g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
• PKA: -3.52±0.40(Predicted)
• CAS DataBase Reference: 5-O-Triphenylmethyl-2-deoxy-2,3-didehyrothymidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-Triphenylmethyl-2-deoxy-2,3-didehyrothymidine(25442-42-6)
• EPA Substance Registry System: 5-O-Triphenylmethyl-2-deoxy-2,3-didehyrothymidine(25442-42-6)

Safety Data

• Hazardous Substances Data: 25442-42-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
5-O-Triphenylmethyl-2-deoxy-2,3-didehyrothymidine is used as a synthetic intermediate for the development of new pharmaceutical compounds. Its unique chemical structure allows for the creation of a wide range of molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-O-Triphenylmethyl-2-deoxy-2,3-didehyrothymidine is used as a key component in the synthesis of therapeutic agents. Its versatility in organic synthesis enables the development of novel drugs with improved efficacy and reduced side effects.
Used in Research and Development:
5-O-Triphenylmethyl-2-deoxy-2,3-didehyrothymidine is also utilized in research and development laboratories for the study of various chemical reactions and the exploration of new synthetic pathways. Its unique properties make it an essential tool for scientists working on the design and synthesis of new molecules with potential applications in medicine and other fields.

Upstream product

• 7791-71-1 5'-O-tritylthymidine 
• 42214-24-4 1-(2-deoxy-3-O-methanesulfonyl-5-O-trityl-β-D-ribopentofuranosyl)thymine 
• 25442-44-8 1-(3'-iodo-2',3'-dideoxy-5'-O-trityl-β-D-erythro-pentofuranosyl)thymine 
• 76-83-5 trityl chloride 
• 50-89-5 thymidine 
• 95585-76-5 2'-bromothymidine 
• 64-17-5 ethanol 
• 131933-43-2 3'-α-(phenylselenyl)-5'-O-trityl-3'-deoxythymidine 

Downstream Products

• 1031759-50-8 5'-O-trityl-3'-S-methoxybenzyl-3'-thiothymidine 
• 108441-77-6 2-ethoxy-1-(2-deoxy-5-O-trityl-β-D-threofuranosyl)thymine 
• 131933-43-2 3'-α-(phenylselenyl)-5'-O-trityl-3'-deoxythymidine 
• 55612-11-8 5'-O-trityldeoxyxylothymidine 
• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 135197-63-6 3'-Fluoro-5'-O-trityl-deoxythymidine 
• 25526-93-6 alovudine 
• 29706-84-1 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine 
• 188559-43-5 5'-O-trityl-O²,3'-cycloanhydro-N³-thymidine 
• 70465-86-0 3'-(ethylthio)-3'-deoxythymidine 
• 596116-37-9 N₁-[1-{4-hydroxy-5-[(trityloxy)methyl]tetrahydro-2-furanyl}-5-methyl-4-oxo-1,4-dihydro-2-pyrimidinyl]-4-methyl-1-benzenesulfonamide 
• 491837-25-3 S-ethyl-5'-O-mesyl-3'-thiothymidine 
• 491837-26-4 S-ethyl-5'-phthalimido-3'-thio-5'-deoxythymidine 
• 124355-25-5 3'-amino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine 

Relevant articles and documents

A new reagent for the formation of anhydronucleosides

5'-O-Trityl-thymidine reacts with excess perfluorobutanesulfonyl fluoride/DBU in toluene to 5'-O-trityl-2,3'-anhydrothymidine in 75% yield. Free thymidine gives rise to 4',5'-dehydro-2,3'-anhydrothymidine and to 5'-fluoro-2,3'-anhydrothymidine.

Intermediate preparation zidovudines and method

Disclosed is a method for preparing zidovudine (B). The method comprises the following steps: 1) 2'-halothymidine (A) is used as the raw material to obtain a compound of formula (I) by protecting the hydroxyl group thereof in the 5'-position; 2) the compound of formula (I) is subjected to the acylation of the hydroxyl group in the 3'-position to obtain a compound of formula (VI); 3) the compound of formula (VI) is dehalogenated to obtain a compound of formula (111); 4) the compound of formula (III) is subjected to an elimination reaction to obtain a compound of formula (IV); 5) the compound of formula (IV) is subjected to an azidation reaction to obtain a compound of formula (V); and 6) the compound of formula (V) is deprotected to obtain zidovudine (B); the specific reaction formula being shown in (C)below. In the formulae: X is a halogen, P1 is a protecting group for hydroxyl; and P2 is C1-C4 alkylsulfonyl, fluoro-C1-C4 alkylsulfonyl, arylsulfonyl or -CS-R, wherein R is C1-C4 alkyl.

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.

Synthesis and evaluation of thymidine-5′-O-monophosphate analogues as inhibitors of Mycobacterium tuberculosis thymidylate kinase

A number of 2′- and 3′-modified thymidine 5′-O-monophosphate analogues were synthesized as potential leads for new anti-mycobacterial drugs. Evaluation of their affinity for Mycobacterium tuberculosis thymidine monophosphate kinase showed that a 2′-halogeno substituent and a 3′-azido function are the most favorable leads for further development of potent inhibitors of this enzyme.

A facile one-pot synthesis of 2,3'-anhydro-2'-deoxyuridines via 3'-O-imidazolylsulfonates

Continued interests in the novel synthetic methods of the pivotal compound, 2,3'-anhydro-2'-deoxyribonucleosides (7) uncovered a facile one-pot conversion of 5 with 1,1'-sulfonyldiimidazole in basic conditions to 7 with almost quantitative yields (91-99%).

Nucleophilic N1→N3 rearrangement of 5′-O-trityl-O2,3′-cycloanhydrothymidine

5′-O-Trityl-O2,3′-cycloanhydrothymidine (1) heated at 150°C in the presence of O,O-diethyl phosphate or O,O-diethyl phosphorothioate anions undergoes rearrangement into N3-isomer (2); its structure was established by both advanced NMR methods and X-ray crystallographic studies. The most probable mechanism of 1 → 2 rearrangement relies upon reversibility of glycosidic bond cleavage process.

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.

Darstellung und Charakterisierung von Trifluormethylchalkogenyl substituierten Nucleosiden

5-Trifluoromethylchalcogenyl-substituted 2'-desoxy-uridines and -cytidines have been synthesized from 2-desoxy-3,5-di-O-(4-methylbenzoyl)-α-D-ribofuranosyl chloride and CF3E-substituted (E=S, SO2, Se) silylated pyrimidines by a modified Hilbert-Johnson reaction.By choosing proper reaction conditions β-anomers may be obtained as the main product.The nucleoside are deprotected by basic transesterification with NH3/CH3OH.After recrystallization from H2O/C2H5OH, 5-trifluoromethylchalcogenyl-2'-desoxynucleosides are formed in good yields.Systematically studiedsubstitution reactions on 5-trifluoromethylsulfanyl-2'-desoxyuridine are described. 5-Trifluoromethylsulfanyl-2',3'-didesoxyuridine is formed by Barton desoxygenation.For the first time, CF3S substitutions at the sugar part of a nucleoside are described.