104218-44-2

Basic information

• Product Name: 3''-O-MESYL-5''-O-TRITYLTHYMIDINE
• Synonyms: 3''-O-MESYL-5''-O-TRITYLTHYMIDINE;1-(3-mesyloxy-5-trityloxymethyl-2-D-threofuryl)thymine
• CAS NO: 104218-44-2
• Molecular Formula: C₃₀H₃₀N₂O₇S
• Molecular Weight: 562.64
• EINECS: 406-360-9
• Mol File: 104218-44-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3''-O-MESYL-5''-O-TRITYLTHYMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 3''-O-MESYL-5''-O-TRITYLTHYMIDINE(104218-44-2)
• EPA Substance Registry System: 3''-O-MESYL-5''-O-TRITYLTHYMIDINE(104218-44-2)

Safety Data

• Statements: 53
• Safety Statements: 61
• Hazardous Substances Data: 104218-44-2(Hazardous Substances Data)

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 55612-11-8 5'-O-trityldeoxyxylothymidine 
• 76-83-5 trityl chloride 
• 7791-71-1 5'-O-tritylthymidine 
• 141690-73-5 3'-Tosyl-5'-O-trityl thymidine 
• 50-89-5 thymidine 
• 52486-19-8 1-(β-D-xylofuranosyl)-thymine 
• 16053-52-4 threothymidine 

Downstream Products

• 5964-41-0 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl-5-O-trityl)thymine 
• 153907-28-9 5-Methyl-1-((2R,4S,5S)-4-propylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 805236-59-3 5'-O-trityl-3'-(acetylthio)-2',3'-dideoxythymidine 
• 135197-63-6 3'-Fluoro-5'-O-trityl-deoxythymidine 
• 29706-84-1 1-(3-azido-2,3-deoxy-5-O-trityl-β-D-erythro-pentofuranosyl)thymine 
• 153907-25-6 5-Methyl-1-((2R,4S,5S)-4-methylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione 
• 153907-27-8 1-((2R,4S,5S)-4-Ethylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 153907-26-7 1-((2R,4S,5S)-4-Dimethylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 153907-29-0 1-((2R,4S,5S)-4-Isopropylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 153907-30-3 1-((2R,4S,5S)-4-Allylamino-5-trityloxymethyl-tetrahydro-furan-2-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 153907-32-5 1-[(2R,4S,5S)-4-(4-Fluoro-benzylamino)-5-trityloxymethyl-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 153907-31-4 3'-benzylamino-3'-deoxy-5'-O-triphenylmethyl-β-D-thymidine 
• 94919-65-0 1-(2-deoxy-3-O-mesyl-β-D-threo-pentofuranosyl)thymine 
• 805236-62-8 Benzoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-prop-2-ynylsulfanyl-tetrahydro-furan-2-ylmethyl ester 

Relevant articles and documents

Solid-phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences

Positively charged DNG oligonucleotide mixed sequences containing A/T bases were prepared by solid-phase synthesis. Synthesis proceeds in 3′→5′ direction and involves coupling of 3′-Fmoc protected thiourea in the presence of HgCl2/TEA with the corresponding 5′-amine of the growing oligo chain. DNG binding characteristics with complementary DNA and with itself have been evaluated.

New nucleoside heteroanalogues: Desoxynucleoside selenocyanates

New nucleoside heteroanalogues, 5' and 3'-desoxynucleoside selenocyanates and primary desoxysugar selenocyanates, were synthesized from activated nucleoside and sugar derivatives and a new convenient seleno nucleophile, tetrabutylammonium selenocyanate. Tresylate-based activation of hydroxy functions turned out to be most successful for formation of theme selenocyanates compared with mesylate- or triflate-based activation.

Process for the deoxygenation of nucleosides

An efficient process for the deoxygenation of 2'- and or 3'-hydroxyl groups of a nucleoside that includes reacting the hydroxyl group with 3-halopropionitrile or 2-nitroethylhalide and carbon disulfide in base to form a 2'- or 3'-(cyanoethylthio or nitroethylthio)thiocarbonyl, that is reductively eliminated and replaced with hydrogen. The deoxygenation process can be used in a wide variety of nucleoside syntheses that require the elimination of the 2'- or 3'-hydroxyl groups, including the preparation of 3'-substituted-2',3'-dideoxynucleosides such as 3'-azido-3'-deoxythymidine and 3'-azido-2',3'-dideoxyuridine.

Synthesis of 3'-fluoro-3'-deoxythymidine and studies of its 18F-radiolabeling, as a tracer for the noninvasive monitoring of the biodistribution of drugs against AIDS

3'-Fluoro-3'-deoxy-thymidine (FDT), a fluorinated analog of 3'-azido-thymidine (AZT), is both more active against the HIV virus but also more toxic than AZT.Because of its fluorine atom, it can be labeled with 18F to be used to monitor this drug's biodistribution and targeting.A new synthesis for FDT, suited for 18F labeling, has been developed.After protecting the 5'-hydroxy group with a trityl group, the 3'-hydroxy group was substituted with a mesyl group in the lyxo configuration.Treatment with 18F potassium fluoride and crown-18 ether yielded the 18F-labeled fluoro derivative which on detritylation afforded 18F FDT with 7percent labeling efficiency.This is the first reported synthesis of 3'-fluoro-5'-O-trityl deoxythymidine using potassium fluoride and preparing its 18F labeled analog.The time required to incorporate 18F in the intermediate compound and isolate the end-product is reasonably short (approximately 2 h) which will allow sufficient time to conduct biological studies with this short-lived radionuclide.

Chemical process

This invention relates to a new synthetic process for the manufacture of zidovudine from the starting material D-xylose involving: i) Conversion of D-xylose to a 1-(β-D-xylofuranosyl)thymine derivative; ii) 2?-Deoxygenation of the thymine derivative; and iii) 3?-Azidation of the 2?-deoxy compound.

SYNTHESIS OF CHEMICALLY REACTIVE ANALOGUES OF AZT AND THEIR BIOLOGICAL EVALUATION AGAINST HIV

Several 3'-deoxythymidine analogues were prepared and tested against HIV.The choice of analogues was based on their possible covalent binding to the enzyme reverse transcriptase.