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
• Article Data: 13

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

Description

5-O-Triphenylmethyl-2-deoxy-2,3-didehyrothymidine, also known as 5-O-Trityl-2,3’-anhydrothymidine (CAS# 25442-42-6), is a white solid compound with significant utility in the field of organic synthesis. It is characterized by its unique chemical structure, which makes it a valuable intermediate for the development of various pharmaceutical compounds.

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 
• 76-83-5 trityl chloride 
• 95585-76-5 2'-bromothymidine 
• 50-89-5 thymidine 
• 64-17-5 ethanol 
• 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 
• 131933-43-2 3'-α-(phenylselenyl)-5'-O-trityl-3'-deoxythymidine 

Downstream Products

• 188559-43-5 5'-O-trityl-O²,3'-cycloanhydro-N³-thymidine 
• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 65-71-4 thymin 
• 148665-49-0 3'-N''-(3'''-azido-3'''-deoxythymid-3''-yl)-3'-deoxythymidine 
• 1031759-50-8 5'-O-trityl-3'-S-methoxybenzyl-3'-thiothymidine 
• 3056-17-5 stavudin 
• 5964-41-0 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine 
• 131933-44-3 1-(2,3-dideoxy-3-C-selenophenyl-β-D-erythro-pentofuranosyl)thymine 
• 66323-49-7 3'-amino-2',3'-dideoxyaguanosine 
• 52450-18-7 3'-amino-3'-deoxythymidine 
• 125944-11-8 9-(3'-amino-2',3'-dideoxy-β-D-ribofuranosyl)adenine 
• 204688-10-8 3'-deoxy-3'-(thymin-1-yl)thymidine 
• 204688-09-5 3'-deoxy-3'-(uracil-1-yl)thymidine 
• 227084-00-6 1-((E)-3-Ethoxy-acryloyl)-3-[(2S,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-trityloxymethyl-tetrahydro-furan-3-yl]-urea 

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.

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.

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%).